2H-benzotriazole UV absorbers substituted with 1,1-diphenylakyl groups and compositions stabilized therewith

ABSTRACT

2H-Benzotriazole UV absorbers substituted at the 3-position or at the 5-position of the phenyl ring by a 1,1-diphenylalkyl moiety, particularly a 1,1-diphenylethyl group, are particularly photostable in automotive coatings, and are of low color and exhibit low volatility in thermoplastic compositions.

[0001] The instant invention pertains to 2H-benzotriazoles substitutedon the phenyl ring at the 3-position or at the 5-position by a1,1-diphenylalkyl moiety.

BACKGROUND OF THE INVENTION

[0002] One of the most important classes of UV absorbers are the2H-benzotriazoles. There are a myriad of patents and other references tothese materials and their compositions. Indeed, several of the2H-benzotriazole UV absorbers have achieved great commercial importancefor a host of end-use applications.

[0003] Benzotriazole UV absorbers which are substituted at the5-position of the benzo ring by an electron withdrawing group exhibitenhanced durability and very low loss rates when incorporated intoautomotive coatings. This is particularly the case when the 3-positionof the phenyl ring is also substituted by phenyl or phenylalkyl such asα-cumyl. Compounds where the 5-position of the benzo ring aresubstituted by perfluoroalkyl such as trifluoromethyl are particularlyof interest for both their enhanced durability and for their excellentsolubility and excellent color properties in some thermoplasticcompositions when the phenyl ring is substituted at the 3-position byhydrogen or tert-alkyl.

[0004] It is well known that the stabilization and other physicalproperties exhibited by the 2H-benzotriazole UV absorbers can bemarkedly altered depending on the nature and location of the varioussubstituents used to modify the basic 2H-benzotriazole structure. Theuse of the substituent 1,1-diphenylalkyl (particularly1,1-diphenylethyl) on the basic benzotriazole molecule is unknown.

[0005] U.S. Pat. No. 5,438,142 and D. Kuila et al. in ChemicalMaterials, 1999 (11), 109 do describe tris(hydroxyphenyl)ethanebenzotriazoles as copolymerizable UV absorbers. The product described inthese references is1-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]-1,1-bis(4-hydroxyphenyl)ethane.The purpose of the two hydroxyphenyl groups at the 4-position of thehydroxylphenyl ring of the 2H-benzotriazole moiety is to providereactive hydroxy groups that can be copolymerized into condensationpolymer systems to provide a non-migrating UV absorbing moiety. The4-hydroxyphenyl moieties of these compounds are substituted at the5-position rather than at the 3-position of the hydroxyphenyl ring ofthe 2H-benzotriazole molecules. As seen from the discussion above, theexact location of the substituent is important when considerations oflong term photostability is concerned.

DETAILED DISCLOSURE

[0006] The instant invention pertains to novel benzotriazole UVabsorbers having enhanced stability and durability and a low loss ratewhen incorporated into automotive coatings. These new benzotriazole UVabsorbers are also soluble in a variety of substrates includingthermoplastic polymers and often are essentially colorless even thoughabsorbing in the 350-390 nm range.

[0007] More specifically, the instant invention pertains to newbenzotriazole compounds of formula I, II or III

[0008] wherein

[0009] G₁ is hydrogen or chloro,

[0010] G₂ is hydrogen, cyano, perfluoroalkyl of 1 to 12 carbon atoms,halogen, —CO—G₃, —COOG₃, —CONHG₃, —CON(G₃)₂, E₃SO—, E₃SO₂—, nitro,—P(O)(C₆H₅)₂, —P(O)(OG₃)₂,

[0011] G₃ is hydrogen, straight or branched chain alkyl of 1 to 24carbon atoms, straight or branched chain alkenyl of 2 to 18 carbonatoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbonatoms, phenyl, or said phenyl or said phenylalkyl substituted on thephenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms,

[0012] E₁ is hydrogen, straight or branched chain alkyl of 1 to 24carbon atoms, straight or branched chain alkenyl of 2 to 24 carbonatoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbonatoms, phenyl, or said phenyl or said phenylalkyl substituted on thephenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms; or E₁ is alkyl of 1to 24 carbon atoms substituted by one or two hydroxy groups;

[0013] or E₁ is alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 18 carbonatoms, said alkyl or said alkenyl substituted by one or more —OCOE₁₁,—OE₄, —NCO, —NHCOE₁₁, or —NE₇E₈, or mixtures thereof, where E₄ isstraight or branched chain alkyl of 1 to 24 carbon atoms or straight orbranched chain alkenyl of 2 to 18 carbon atoms; or said alkyl or saidalkenyl interrupted by one or more —O—, —NH— or —NE₄— groups or mixturesthereof and which can be unsubstituted or substituted by one or more—OH, —OE₄ or —NH₂, or mixtures thereof;

[0014] or E₁ is a group of formula IV

[0015] where

[0016] E₂₂, E₂₃, E₂₄, E₂₅, E₂₆, E₂₈, E₂₉, E₃₀, E₃₁ and E₃₂ areindependently hydrogen, halogen, straight or branched alkyl of 1 to 18carbon atoms, alkenyl of 2 to 18 carbon atoms, said alkyl or saidalkenyl substituted by one or more halogen, —OCOE₁₁, —OE₄, —NCO,—NHCOE₁₁ or —NE₇E₈, or mixtures thereof, where E₄ is straight orbranched chain alkyl of 1 to 24 carbon atoms or straight or branchedchain alkenyl of 2 to 18 carbon atoms; or said alkyl or said alkenylinterrupted by one or more —O—, —NH— or —NE₄— groups or mixtures thereofand which can be unsubstituted or substituted by one or more —OH, —OE₄or —NH₂, or mixtures thereof; or E₂₂, E₂₃, E₂₄, E₂₅, E₂₆, E₂₈, E₂₉, E₃₀,E₃₁ and E₃₂ are independently phenyl, —OH, —OCOE₁₁, —OE₃₃, —NCO,—NHCOE₁₁ or —NE₇E₈, cyano, nitro, perfluoroalkyl of 1 to 12 carbonatoms, —COG₃, —COOG₃, —CON(G₃)₂, —CONHG₃, E₃S—, E₃SO—, E₃SO₂—,—P(O)(C₆H₅)₂, —P(O))OG₃)₂, —SO₂—X₁—E₃₃;

[0017] X₁ is —O—, —NH— or —NE₄—;

[0018] E₂₇ is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12carbon atoms or phenyl,

[0019] E₃₃ is straight or branched chain alkyl of 1 to 24 carbon atoms,straight or branched chain alkenyl of 2 to 18 carbon atoms, said alkylor said alkenyl substituted by one or more —OH, —OCE₁₁, —OE₄, —NCO,—NHCOE₁₁, —NE₇E₈, phthalimido,

[0020] or mixtures thereof, where E₄ is straight or branched chain alkylof 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms; or saidalkyl or said alkenyl interrupted by one or more —O—, —NH— or —NE₄—groups or mixtures thereof and which can be unsubstituted or substitutedby one or more —OH, —OE₄ or —NH₂, or mixtures thereof; or E₃₃ is phenylor phenylalkyl of 7 to 15 carbon atoms, or said phenyl or saidphenylalkyl substituted by one to three alkyl groups of 1 to 4 carbonatoms;

[0021] E₂ is straight or branched alkyl chain of 1 to 24 carbon atoms,straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkylof 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, orsaid phenyl or said phenylalkyl substituted on the phenyl ring by one tothree alkyl of 1 to 4 carbon atoms; or E₂ is alkyl of 1 to 24 carbonatoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more—OH, —OCOE₁₁, —OE₄, —NCO, —NH₂, —NHCOE₁₁, —NHE₄ or —N(E₄)₂, or mixturesthereof, where E₄ is straight or branched chain alkyl of 1 to 24 carbonatoms; or said alkyl or said alkenyl interrupted by one or more —O—,—NH— or —NE₄— groups or mixtures thereof and which can be unsubstitutedor substituted by one or more —OH, —OE₄ or —NH₂ groups or mixturesthereof; or E₂ is a group of formula IV described above;

[0022] n is 1 or 2,

[0023] when n is 1, E₅ is OE₆ or NE₇E₈, or

[0024] E₅ is —PO(OE₁₂)₂, —OSi(E₁₁)₃ or —OCO—E₁₁, or straight or branchedchain C₁-C₂₄alkyl which is interrupted by —O—, —S— or —NE₁₁ and whichcan be unsubstituted or substituted by —OH or —OCO—E₁₁, C₅-C₁₂cycloalkyl which is unsubstituted or substituted by —OH, straight chainor branched C₂-C₁₈alkenyl which is unsubstituted or substituted by —OH,C₇-C₁₅aralkyl, —CH₂—CHOH—E₁₃ or glycidyl,

[0025] E₆ is hydrogen, straight or branched chain C₁-C₂₄alkyl which isunsubstituted or substituted by one or more OH, OE₄ or NH₂ groups, or—OE₆ is —(OCH₂CH₂)_(w)OH or —(OCH₂CH₂)WOE₂₁ where w is 1 to 12 and E₂,is alkyl of 1 to 12 carbon atoms, E₇ and E₈ are independently hydrogen,alkyl of 1 to 18 carbon atoms, straight or branched chain C₃-C₁₈alkylwhich is interrupted by —O—, —S— or —NE₁₁—, C₅-C₁₂cycloalkyl, C₆-C₁₄arylor C₁-C₃hydroxylalkyl, or E₇ and E₈ together are alkylene of 4 to 6carbon atoms, 3-oxapentamethylene, 3-iminopentamethylene or3-methyliminopentamethylene, or

E₅ is —X—(Z)_(p)—Y—E₁₅

[0026] wherein

[0027] X is —O— or —N(E₆)—,

[0028] Y is −O— or —N(E₁₇)—,

[0029] Z is C₂-C₁₂-alkylene, C₄-C₁₂-alkylene interrupted by one to threenitrogen atoms, oxygen atoms or a mixture thereof, or isC₃-C₁₂-alkylene, butenylene, butynylene, cyclohexylene or phenylene,each substituted by a hydroxyl group,

[0030] m is zero, 1 or 2,

[0031] p is 1, or p is also zero when X and Y are —N(E₁₆)— and —N(E₁₇)—,respectively,

[0032] E₁₅ is a group —CO—C(E₁₈)═C(H)E₁₉ or, when Y is —N(E₁₇)—, formstogether with E₁₇ a group —CO—CH═H—CO—, wherein E₁₈ is hydrogen ormethyl, and E₁₉ is hydrogen, methyl or —CO—X—E₂₀, wherein E₂₀ ishydrogen, C₁-C₁₂-alkyl or a group of the formula

[0033] wherein the symbols E₁, G₂, X, Z, m and p have the meaningsdefined above, and E₁₆ and E₁₇ independendy of one another are hydrogen,C₁-C₁₂-alkyl, C₃-C₁₂-alkyl interrupted by 1 to 3 oxygen atoms, or iscyclohexyl or C₇-C₁₅aralkyl, and E₁₆ together with E₁₇ in the case whereZ is ethylene, also forms ethylene,

[0034] when n is 2, E₅ is one of divalent radicals —O—E₉—O— or—N(E₁₁)—E₁₀—N(E₁₁)—,

[0035] E₉ is C₂-C₈alkylene, C₄-C₈alkenylene, C₄alkynylene,cyclohexylene, straight or branched chain C₄-C₁₀alkylene which isinterrupted by —O— or by —CH₂—CHOH—CH₂—O—E₁₄—O—CH₂—CHOH—CH₂—,

[0036] E₁₀ being straight or branched chain C₂-C₁₂alkylene which may beinterrupted by —O—, cyclohexylene, or

[0037] or E₁₀ and E₁₁ with the two nitrogen atoms form a piperazinering,

[0038] E₁₄ is straight or branched chain C₂-C₈alkylene, straight orbranched chain C₄-C₁₀alkylene which is interrupted by —O—,cycloalkylene, arylene or

[0039] E₁₁ is hydrogen, straight or branched chain C₁-C₁₈alkyl,C₅-C₁₂cycloalkyl, straight or branched chain C₂-C₁₈alkenyl, C₆-C₁₄arylor C₇-C₁₅aralkyl,

[0040] E₁₂ is straight or branched chain C₁-C₁₈alkyl, straight orbranched chain C₃-C₁₈alkenyl, C₅-C₁₀Cycoalkyl, C₆-C₁₆aryl orC₇-C₁₅aralkyl,

[0041] E₁₃ is H, straight chain or branched C₁-C₁₈alkyl which issubstituted by —PO(OE₁₂)₂, phenyl which is unsubstituted or substitutedby OH, C₇-C₁₅aralkyl or —CH₂OE₁₂,

[0042] E₃ is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10carbon atoms or said aryl substituted by one or two alkyl of 1 to 4carbon atoms or 1,1,2,2-tetrahydroperfluoroalkyl where theperfluoroalkyl moiety is of 6 to 16 carbon atoms,

[0043] T is —SO—, —SO₂—, —SO—E—SO—, —SO₂—E—SO₂—, —CO—, —CO—CO—,—CO—CH₂—CO—, —CO—E—CO—, —COO—E—OCO— or —CO—NG₅—E—NG₅—CO—,

[0044] where E is alkylene of 2 to 12 carbon atoms, cycloalkylene of 5to 12 carbon atoms, or alkylene interrupted or terminated bycyclohexylene of 8 to 12 carbon atoms;

[0045] G₅ is G₃ or hydrogen, and

[0046] with the proviso that at least one of E₁ and E₂ must contain agroup of formula IV; and

[0047] with the further proviso that when E₂₄ and E₃₀ are OH, G₂ is nothydrogen.

[0048] Preferably, the new benzotriazole is a compound of formula I

[0049] wherein

[0050] G₁ is hydrogen,

[0051] G₂ is hydrogen, cyano, CF₃—, fluoro, chloro, —CO—G₃, —COOG₃ orE₃SO₂—,

[0052] G₃ is straight or branched chain alkyl of 1 to 24 carbon atoms,straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkylof 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, orsaid phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4alkyl of 1 to 4 carbon atoms, E₁ is a group of formula IV wherein E₂₂,E₂₃, E₂₄, E₂₅, E₂₆, E₂₈, E₂₉, E₃₀, E₃₁ and E₃₂ are hydrogen, and E₂₇ ismethyl,

[0053] E₂ is straight or branched alkyl chain of 1 to 24 carbon atoms,straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkylof 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, orsaid phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3alkyl of 1 to 4 carbon atoms; or E₂ is said alkyl of 1 to 24 carbonatoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more—OH, —OCOE₁₁, —OE₄, —NCO, —NH₂, —NHCOE₁₁, —NHE₄ or —N(E₄)₂, or mixturesthereof, where E₄ is straight or branched chain alkyl of 1 to 24 carbonatoms; or said alkyl or said alkenyl interrupted by one or more —O—,—NH— or —NE₄— groups or mixtures thereof and which can be unsubstitutedor substituted by one or more —OH, —OE₄ or —NH₂ groups or mixturesthereof, or E₂ is a group of formula IV wherein E₂₂, E₂₃, E₂₄, E₂₅, E₂₆,E₂₈, E₂₉, E₃₀, E₃₁ and E₃₂ are hydrogen, alkyl of 1 to 12 carbon atoms,straight or branched chain alkenyl of 2 to 18 carbon atoms, OH, cyano,—OE₃₃, chloro, fluoro, —OCOE₁₁, CF₃, —COOG3, E₃S—, E₃SO₂— or—SO₂—NH—E₃₃; and E₂₇ is methyl,

[0054] E₃ is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10carbon atoms or said aryl substituted by one or two alkyl of 1 to 4carbon atoms or 1,1,2,2-tetrahydroperfluoroalkyl where theperfluoroalkyl moiety is of 6 to 16 carbon atoms; and wherein E₁₁ andE₃₃ are as defined above.

[0055] Most preferably, the instant compounds of formula I are

[0056] (a)2-[2-hydroxy-3-(1,1-diphenylethyl)-5-tert-butylphenyl]-2H-benzotriazole;

[0057] (b)5-chloro-2-[2-hydroxy-3-(1,1-diphenylethyl)-5-tert-butylphenyl]-2H-benzo-triazole;or

[0058] (c)5-trifluoromethyl-2-[2-hydroxy-3-(1,1-diphenylethyl)-5-tert-octylphenyl]-2H-benzotriazole.

[0059] The instant invention also pertains to a composition stabilizedwhich comprises

[0060] (a) an organic material subject to degradation by heat, light oroxygen, and

[0061] (b) an effective stabilizing amount of a compound of formula I,II or II as described above.

[0062] Preferably, the organic material is a natural, semi-synthetic orsynthetic polymer, especially a thermoplastic polymer.

[0063] Most preferably, the polymer is a polyolefin or polycarbonate,especially polyethylene or polypropylene; most especially polypropylene;or the polymer is a styrenic, ABS, a nylon, a polyester such aspoly(ethylene terephthalate) or poly(butylene terephthalate), apolyurethane, an acrylate, a rubber modified styrenic, poly(vinylchloride), poly(vinyl butyral), polyacetal (polyoxymethylene),poly(ethylene naphthalene-dicarboxylate), or other blends or copolymerssuch as poly(ethylene/1,4-cyclohexylene-dimethylene terephthalate) PETGor an ionomer as described on page 29.

[0064] In another preferred embodiment of the instant invention, theorganic material is a resin selected from the group consisting of athermoset acrylic melamine resin, an acrylic urethane resin, an epoxycarboxy resin, a silane modified acrylic melamine, an acrylic resin withcarbamate pendant groups crosslinked with melamine or an acrylic polyolresin crosslinked with melamine containing carbamate groups.

[0065] Most preferably, the resin is a thermoset acrylic melamine resinor an acrylic urethane resin.

[0066] In yet another preferred embodiment of the instant invention, theorganic material is a recording material.

[0067] The recording materials according to the invention are suitablefor pressure-sensitive copying systems, photocopying systems usingmicrocapsules, heat-sensitive copying systems, photographic materialsand ink jet printing.

[0068] The recording materials according to the invention aredistinguished by an unexpected improvement in quality, especially withregard to the fastness to light.

[0069] The recording materials according to the invention have theconstruction known for the particular use. They consist of a customarycarrier, for example, paper or plastic film, which has been coated withone or more layers. Depending on the type of material, these layerscontain the appropriate necessary components, in the case ofphotographic materials, for example, silver halide emulsions, dyecouplers, dyes and the like. Material particularly suitable for ink jetprinting has a layer particularly absorptive for ink on a customarycarrier. Uncoated paper can also be employed for ink jet printing. Inthis case the paper acts at the same time as the carrier material and asthe ink-absorbent layer. Suitable material for ink jet printing is, forexample, described in U.S. Pat. No. 5,073,448 which is incorporatedherein by reference.

[0070] The recording material can also be transparent as, for example,in the case of projection films.

[0071] The compounds of formula I, II or III can be incorporated intothe carder material as early as the production of the latter, in theproduction of paper, for example, being added to the paper pulp. Asecond method of application is to spray the carder material with anaqueous solution of compounds of formula I, II or III or to add thecompounds to the coating composition.

[0072] Coating compositions intended for transparent recording materialssuitable for projection cannot contain any particles which scatterlight, such as pigments and fillers.

[0073] The dye-binding coating composition can contain a number of otheradditives, for example, antioxidants, light stabilizers (including alsoUV absorbers which do not fall under the scope of the UV absorbers ofthis invention), viscosity improvers, fluorescent brighteners, biocidesand/or antistatic agents.

[0074] The coating composition is usually prepared as follows: thewater-soluble components, for example, the binder, are dissolved inwater and stirred together; the solid components, for example, fillersand other additives already described, are dispersed in this aqueousmedium; and disperison is advantageously carried out by means ofdevices, for example, ultrasonic systems, turbine stirrers,homogenizers, colloid mills, bead mills, sand mills, high-speed stirrersand the like. The compounds of formula I, II or III can be easilyincorporated into the coating composition.

[0075] The recording material according to this invention preferablycontains 1 to 5000 mg/m², in particular 50-1200 mg/m², of a compound offormula I, II or III.

[0076] As already mentioned, the recording materials according to theinvention embrace a wide field. The compounds of formula I, II or IIIcan, for example, be employed in pressure-sensitive copying systems.They can be introduced either into the paper in order to protect themicroencapsulated dye precursors there from light, or into the binder ofthe developer layer in order to protect the dyes formed there.

[0077] Photocopying systems using light-sensitive microcapsules whichare developed by means of pressure are described in U.S. Pat. Nos.4,416,966; 4,483,912; 4,352,200; 4,535,050; 4,535,463; 4,551,407;4,562,137 and 4,608,330; and also in EP-A 139,479; EP-A 162,664; EP-A164,931; EP-A 237,024; EP-A 237,025 and EP-A 260,129. In all thesesystems, the compounds can be put into the dye-receiving layer. Thecompounds can, however, also be put into the donor layer in order toprotect the color formers from light.

[0078] Photographic materials which can be stabilized are photographicdyes and layers containing such dyes or precursors thereof, for example,photographic paper and films. Suitable materials are, for example,described in U.S. Pat. No. 5,364,749 which is incorporated herein byreference. The compounds of formula I, II or III act here as a UV filteragainst electrostatic flashes. In color photographic materials, couplersand dyes are also protected against photochemical decomposition.

[0079] The instant compounds can be used for all types of colorphotographic materials. For example, they can be employed for colorpaper, color reversal paper, direct-positive color material, colornegative film, color positive film, color reversal film and the like.They are preferably used inter alia for photographic color materialwhich contains a reversal substrate or form positives.

[0080] Color-photographic recording materials usually contain, on asupport, a blue-sensitive and/or a green-sensitive and/or ared-sensitive silver halide emulsion layer and, if desired, a protectionlayer, with the instant compounds being, preferably, either in thegreen-sensitive or the red-sensitive layer or in a layer between thegreen-sensitive and the red-sensitive layer or in a layer on top of thesilver halide emulsion layers.

[0081] The compounds of formula I, II or III can also be employed inrecording materials based on the principles of photopolymerization,photoplasticization or the rupture of microcapsules, or in cases whereheat-sensitive and light-sensitive diazonium salts, leuko dyes having anoxidizing agent or dye lactones having Lewis acids are used.

[0082] Furthermore, the instant compounds can be employed in recordingmaterials for dye diffusion transfer printing, thermal wax transferprinting and non-matrix printing and for use with electrostatic,electrographic, electrophoretic, magnetographic andlaser-electrophotographic printers and pen-plotters. Of the above,recording materials for dye diffusion transfer printing are preferred,for example, as described in EP-A 507,734.

[0083] The instant compounds can also be employed in inks, preferablyfor ink jet printing, for example, as described in U.S. Pat. No.5,098,477 which is incorporated herein by reference.

[0084] The instant compounds also are effective in the protection ofdyes present in candle wax from premature degradation and fading.

[0085] The instant compounds of formula I, II or III are also useful inadhesives used in solar films, optical films and other laminatedstructures against the adverse effects of ultraviolet light and actinicradiation.

[0086] The compounds of this invention exhibit superior hydrolyticstability, handling and storage stability as well as good resistance toextractability when present in a stabilized composition.

[0087] The methodology to make the instant compounds is described in theprior art. The intermediates needed to make the instant compounds arelargely items of commerce.

[0088] Preferred compounds are those in which one of X and Y is −O—; andparticularly those in which both X and Y are —O—.

[0089] In general polymers which can be stabilized include

[0090] 1. Polymers of monoolefins and diolefins, for examplepolypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene,polyisoprene or polybutadiene, as well as polymers of cycloolefins, forinstance of cyclopentene or norbornene, polyethylene (which optionallycan be crosslinked), for example high density polyethylene (HDPE), lowdensity polyethylene (LDPE), linear low density polyethylene (LLDPE),branched low density polyethylene (BLDPE).

[0091]  Polyolefins, i.e. the polymers of monoolefins exemplified in thepreceding paragraph, preferably polyethylene and polypropylene, can beprepared by different, and especially by the following, methods:

[0092] a) radical polymerisation (normally under high pressure and atelevated temperature).

[0093] b) catalytic polymerisation using a catalyst that normallycontains one or more than one metal of groups IVb, Vb, VIb or VIII ofthe Periodic Table. These metals usually have one or more than oneligand, typically oxides, halides, alcoholates, esters, ethers, amines,alkyls, alkenyls and/or aryls that may be either π- or σ-coordinatedThese metal complexes may be in the free form or fixed on substrates,typically on activated magnesium chloride, titanium(III) chloride,alumina or silicon oxide. These catalysts may be soluble or insoluble inthe polymerisation medium. The catalysts can be used by themselves inthe polymerisation or further activators may be used, typically metalalkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metalalkyloxanes, said metals being elements of groups Ia, IIa and/or IIIa ofthe Periodic Table. The activators may be modified conveniently withfurther ester, ether, amine or silyl ether groups. These catalystsystems are usually termed Phillips, Standard Oil Indiana, Ziegler(-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).

[0094] 2. Mixtures of the polymers mentioned under 1), for examplemixtures of polypropylene with polyisobutylene, polypropylene withpolyethylene (for example PP/HDPE, PP/LDPE) and mixtures of differenttypes of polyethylene (for example LDPE/HDPE).

[0095] 3. Copolymers of monoolefins and diolefins with each other orwith other vinyl monomers, for example ethylene/propylene copolymers,linear low density polyethylene (ILDPE) and mixtures thereof with lowdensity polyethylene (LDPE), propylene/but-1-ene copolymers,propylene/isobutylene copolymers, ethylene/but-1-ene copolymers,ethylene/hexene copolymers, ethylene/methylpentene copolymers,ethylene/heptene copolymers, ethylene/octene copolymers,propylene/butadiene copolymers, isobutylene/isoprene copolymers,ethylene/alkyl acrylate copolymers, ethylene/alkyl methacrylatecopolymers, ethylene/vinyl acetate copolymers and their copolymers withcarbon monoxide or ethylene/acrylic acid copolymers and their salts(ionomers) as well as terpolymers of ethylene with propylene and a dienesuch as hexadiene, dicyclopentadiene or ethylidene-norbornene; andmixtures of such copolymers with one another and with polymers mentionedin 1) above, for example polypropylene/ethylene-propylene copolymers,LDPE/ethylene-vinyl acetate copolymers (EVA), LDPE/ethylene-acrylic acidcopolymers (EAA), LLDPE/EVA, LLDPE/EAA and alternating or randompolyalkylene/carbon monoxide copolymers and mixtures thereof with otherpolymers, for example polyamides.

[0096] 4. Hydrocarbon resins (for example C₅-C₉) including hydrogenatedmodifications thereof (e.g. tackifiers) and mixtures of polyalkylenesand starch.

[0097] 5. Polystyrene, poly(p-methylstyrene), poly(α-methylstyrene).

[0098] 6. Copolymers of styrene or a-methylstyrene with dienes oracrylic derivatives, for example styrene/butadiene,styrene/acrylonitrile, styrene/alkyl methacrylate,styrene/butadiene/alkyl acrylate, styrene/butadiene/alkyl methacrylate,styrene/maleic anhydride, styrene/acrylonitrile/methyl acrylate;mixtures of high impact strength of styrene copolymers and anotherpolymer, for example a polyacrylate, a diene polymer or anethylene/propylene/diene terpolymer, and block copolymers of styrenesuch as styrene/butadiene/styrene, styrene/isoprene/styrene,styrene/ethylene/butylene/styrene or styrene/ethylene/propylene/styrene.

[0099] 7. Graft copolymers of styrene or α-methylstyrene, for examplestyrene on polybutadiene, styrene on polybutadiene-styrene orpolybutadiene-acrylonitrile copolymers; styrene and acrylonitrile (ormethacrylonitrile) on polybutadiene; styrene, acrylonitrile and methylmethacrylate on polybutadiene; styrene and maleic anhydride onpolybutadiene; styrene, acrylonitrile and maleic anhydride or maleimideon polybutadiene; styrene and maleimide on polybutadiene; styrene andalkyl acrylates or methacrylates on polybutadiene; styrene andacrylonitrile on ethylene/propylene/diene terpolymers; styrene andacrylonitrile on polyalkyl acrylates or polyalkyl methacrylates, styreneand acrylonitrile on acrylate/butadiene copolymers, as well as mixturesthereof with the copolymers listed under 6), for example the copolymermixtures known as ABS, MBS, ASA or AES polymers.

[0100] 8. Halogen-containing polymers such as polychloroprene,chlorinated rubbers, chlorinated or sulfochlorinated polyethylene,copolymers of ethylene and chlorinated ethylene, epichlorohydrin homo-and copolymers, especially polymers of halogen-containing vinylcompounds, for example polyvinyl chloride, polyvinylidene chloride,polyvinyl fluoride, polyvinylidene fluoride, as well as copolymersthereof such as vinyl chloride/vinylidene chloride, vinyl chloride/vinylacetate or vinylidene chloride/vinyl acetate copolymers.

[0101] 9. Polymers derived from α,β-unsaturated acids and derivativesthereof such as polyacrylates and polymethacrylates; polymethylmethacrylates, polyacrylamides and polyacrylonitriles, impact-modifiedwith butyl acrylate.

[0102] 10. Copolymers of the monomers mentioned under 9) with each otheror with other unsaturated monomers, for example acrylonitrile/butadienecopolymers, acrylonitrile/alkyl acrylate copolymers,acrylonitrile/alkoxyalkyl acrylate or acrylonitrile/vinyl halidecopolymers or acrylonitrile/alkyl methacrylate/butadiene terpolymers.

[0103] 11. Polymers derived from unsaturated alcohols and amines or theacyl derivatives or acetals thereof, for example polyvinyl alcohol,polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinylmaleate, polyvinyl butyral, polyallyl phthalate or polyallyl melamine;as well as their copolymers with olefins mentioned in 1) above.

[0104] 12. Homopolymers and copolymers of cyclic ethers such aspolyalkylene glycols, polyethylene oxide, polypropylene oxide orcopolymers thereof with bisglycidyl ethers.

[0105] 13. Polyacetals such as polyoxymethylene and thosepolyoxymethylenes which contain ethylene oxide as a comonomer,polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.

[0106] 14. Polyphenylene oxides and sulfides, and mixtures ofpolyphenylene oxides with styrene polymers or polyamides.

[0107] 15. Polyurethanes derived from hydroxyl-terminated polyethers,polyesters or polybutadienes on the one hand and aliphatic or aromaticpolyisocyanates on the other, as well as precursors thereof

[0108] 16. Polyamides and copolyamides derived from diamines anddicarboxylic acids and/or from aminocarboxylic acids or thecorresponding lactams, for example polyamide 4, polyamide 6, polyamide6/6, 6/10, 6/9, 6/12, 4/6, 12/12, polyamide 11, polyamide 12, aromaticpolyamides starting from m-xylene diamine and adipic acid; polyamidesprepared from hexamethylenediamine and isophthalic or/and terephthalicacid and with or without an elastomer as modifier, for examplepoly-2,4,4,-trimethylhexamethylene terephthalamide or poly-m-phenyleneisophthalamide; and also block copolymers of the aforementionedpolyamides with polyolefins, olefin copolymers, ionomers or chemicallybonded or grafted elastomers; or with polyethers, e.g. with polyethyleneglycol, polypropylene glycol or polytetramethylene glycol; as well aspolyamides or copolyamides modified with EPDM or ABS; and polyamidescondensed during processing (RIM polyamide systems).

[0109] 17. Polyureas, polyimides, polyamide-imides andpolybenzimidazoles.

[0110] 18. Polyesters derived from dicarboxylic acids and diols and/orfrom hydroxycarboxylic acids or the corresponding lactones, for examplepolyethylene terephthalate, polybutylene terephthalate,poly-1,4-dimethylolcyclohexane terephthalate and polyhydroxybenzoates,as well as block copolyether esters derived from hydroxyl-terminatedpolyethers; and also polyesters modified with polycarbonates or MBS.

[0111] 19. Polycarbonates and polyester carbonates.

[0112] 20. Polysulfones, polyether sulfones and polyether ketones.

[0113] 21. Crosslinked polymers derived from aldehydes on the one handand phenols, ureas and melamines on the other hand, such asphenol/formaldehyde resins, urea/formaldehyde resins andmelamine/formaldehyde resins.

[0114] 22. Drying and nondrying alkyd resins.

[0115] 23. Unsaturated polyester resins derived from copolyesters ofsaturated and unsaturated dicarboxylic acids with polyhydric alcoholsand vinyl compounds as crosslinking agents, and also halogen-containingmodifications thereof of low flammability.

[0116] 24. Crosslinkable acrylic resins derived from substitutedacrylates, for example epoxy acrylates, urethane acrylates or polyesteracrylates.

[0117] 25. Alkyd resins, polyester resins and acrylate resinscrosslinked with melamine resins, urea resins, polyisocyanates or epoxyresins.

[0118] 26. Crosslinked epoxy resins derived from polyepoxides, forexample from bisglycidyl ethers or from cycloaliphatic diepoxides.

[0119] 27. Natural polymers such as cellulose, rubber, gelatin andchemically modified homologous derivatives thereof, for examplecellulose acetates, cellulose propionates and cellulose butyrates, orthe cellulose ethers such as methyl cellulose; as well as rosins andtheir derivatives.

[0120] 28. Blends of the aforementioned polymers (polyblends), forexample PP/EPDM, Polyamide/EPDM or ABS, PVC/EVA, PVC/ABS, PVC/MBS,PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acylates,POM/thermoplastic PUR, PC/thermoplastic PUR, POM/acrylate, POM/MBS,PPO/HIPS, PPO/PA 6.6 and copolymers, PA/HDPE, PA/PP, PA/PPO.

[0121] 29. Naturally occurring and synthetic organic materials which arepure monomeric compounds or mixtures of such compounds, for examplemineral oils, animal and vegetable fats, oil and waxes, or oils, fatsand waxes based on synthetic esters (e.g. phthalates, adipates,phosphates or trimellitates) and also mixtures of synthetic esters withmineral oils in any weight ratios, typically those used as spinningcompositions, as well as aqueous emulsions of such materials.

[0122] 30. Aqueous emulsions of natural or synthetic rubber, e.g.natural latex or latices of carboxylated styrene/butadiene copolymers.

[0123] 31. Polysiloxanes such as the soft, hydrophilic polysiloxanesdescribed, for example, in U.S. Pat. No. 4,259,467; and the hardpolyorganosiloxanes described, for example, in U.S. Pat. No. 4,355,147.

[0124] 32. Polyketimines in combination with unsaturated acrylicpolyacetoacetate resins or with unsaturated acrylic resins. Theunsaturated acrylic resins include the urethane acrylates, polyetheracrylates, vinyl or acryl copolymers with pendant unsaturated groups andthe acrylated melamines. The polyketimines are prepared from polyaminesand ketones in the presence of an acid catalyst.

[0125] 33. Radiation curable compositions containing ethylenicallyunsaturated monomers or oligomers and a polyunsaturated aliphaticoligomer.

[0126] 34. Epoxymelamine resins such as light-stable epoxy resinscrosslinked by an epoxy functional coetherified high solids melamineresin such as LSE-4103 (Monsanto).

[0127] In general, the compounds of the present invention are employedin from about 0.01 to about 5% by weight of the stabilized composition,although this will vary with the particular substrate and application.An advantageous range is from about 0.05 to about 3%, and especially0.05 to about 1%. However, some high performance films or in UVabsorbing layers of laminates such as those produced by coextrusion maycontain from 5-15% by weight of the instant compounds. Concentrations of5-10% by weight are typical in certain coextrusion applications.

[0128] The stabilizers of the instant invention may readily beincorporated into the organic polymers by conventional techniques, atany convenient stage prior to the manufacture of shaped articlestherefrom. For example, the stabilizer may be mixed with the polymer indry powder form, or a suspension or emulsion of the stabilizer may bemixed with a solution, suspension, or emulsion of the polymer. Theresulting stabilized polymer compositions of the invention mayoptionally also contain from about 0.01 to about 5%, preferably fromabout 0.025 to about 2%, and especially from about 0.1 to about 1% byweight of various conventional additives, such as the materials listedbelow, or mixtures thereof.

[0129] 1. Antioxidants

[0130] 1.1. Alkylated monophenols, for example,

[0131] 2,6-di-tert-butyl-4-methylphenol

[0132] 2-tert-butyl-4,6-dimethylphenol

[0133] 2,6-di-tert-butyl-4-ethylphenol

[0134] 2,6-di-tert-butyl-4-n-butylphenol

[0135] 2,6-di-tert-butyl-4-1-butylphenol

[0136] 2,6-di-cyclopentyl-4-methylphenol

[0137] 2-(α-methylcyclohexyl)-4,6-dimethylphenol

[0138] 2,6-di-octadecyl-4-methylphenol

[0139] 2,4,6-tri-cyclohexylphenol

[0140] 2,6-di-tert-butyl-4-methoxymethylphenol

[0141] 1.2. Alkylated hydroquinones, for example,

[0142] 2,6-di-tert-butyl-4-methoxyphenol

[0143] 2,5-di-tert-butyl-hydroquinone

[0144] 2,5-di-tert-amyl-hydroquinone

[0145] 2,6-diphenyl-4-octadecyloxyphenol

[0146] 1.3. Hydroxylated thiodiphenyl ethers, for example,

[0147] 2,2′-thio-bis-(6-tert-butyl-4-methylphenol)

[0148] 2,2′-thio-bis-(4-octylphenol)

[0149] 4,4′-thio-bis-(6-tert-butyl-3-methylphenol)

[0150] 4,4′-thio-bis-(6-tert-butyl-2-methylphenol)

[0151] 1.4. Alkylidene-bisphenols, for example,

[0152] 2,2′-methylene-bis-(6-tert-butyl-4-methylphenol)

[0153] 2,2′-methylene-bis-(6-tert-butyl-4-ethylphenol)

[0154] 2,2′-methylene-bis-[4-methyl-6-(α-methylcyclohexyl)-phenol]

[0155] 2,2′-methylene-bis-(4-methyl-6-cyclohexylphenol)

[0156] 2,2′-methylene-bis-(6-nonyl-4-methylphenol)

[0157] 2,2′-methylene-bis-[6-(α-methylbenzyl)4-nonylphenol]

[0158] 2,2′-methylene-bis-[6-(α,α-dimethylbenzyl)-4-nonylphenol]

[0159] 2,2′-methylene-bis-(4,6-di-tert-butylphenol)

[0160] 2,2′-ethylidene-bis-(4,6-di-tert-butylphenol)

[0161] 2,2′-ethylidene-bis-(6-tert-butyl-4-isobutyphenol)

[0162] 4,4′-methylene-bis-(2,6-di-tert-butylphenol)

[0163] 4,4′-methylene-bis-(6-tert-butyl-2-methylphenol)

[0164] 1,1-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-butane

[0165] 2,6-di-(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol

[0166] 1,1,3-tris-(5-tert-butyl-4-hydroxy-2-methylphenyl)-butane

[0167]1,1-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane

[0168] ethyleneglycolbis-[3,3-bis-(3′-tert-butyl-4′-hydroxyphenyl)-butyrate]

[0169] di-(3-tert-butyl-4-hydroxy-5-methylphenyl)-dicyclopentadiene

[0170]di-[2-(3′-tert-butyl-2′-hydroxy-5′-methyl-benzyl)-6-tert-butyl-4-methylphenyl]terephthalate.

[0171] 1.5. Benzyl compounds, for example,

[0172]1,3,5-tri-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene

[0173] di-(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide

[0174] 3,5-di-tert-butyl-4-hydroxybenzyl-mercapto-acetic acid isooctylester

[0175] bis-(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithiolterephthalate

[0176] 1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate

[0177] 1,3,5-tris-(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate

[0178] 3,5-di-tert-butyl-4-hydroxybenzyl-phosphoric acid dioctadecylester

[0179] 3,5-di-tert-butyl-4-hydroxybenzyl-phosphoric acid monoethylester, calcium-salt

[0180] 1.6. Acylaminophenols, for example,

[0181] 4-hydroxy-lauric acid anilide

[0182] 4-hydroxy-stearic acid anilide

[0183]2,4-bis-octylmercapto-6-(3,5-tert-butyl-4-hydroxyanilino)-s-triazine

[0184] octyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)-carbamate

[0185] 1.7. Esters of β-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionicacid with monohydric or polyhydric alcohols, for example, methanoldiethylene glycol octadecanol triethylene glycol 1,6-hexanediolpentaerythritol neopentyl glycol tris-hydroxyethyl isocyanuratethiodiethylene glycol di-hydroxyethyl oxalic acid diamidetriethanolamine triisopropanolamine

[0186] 1.8. Esters ofβ-(5-tert-butyl-4-hydroxy-3-methylphenyl)-propionic acid with monohydricor polyhydric alcohols, for example, methanol diethylene glycoloctadecanol triethylene glycol 1,6-hexanediol pentaerythritol neopentylglycol tris-hydroxyethyl isocyanurate thiodiethylene glycoldi-hydroxyethyl oxalic acid diamide triethanolamine triisopropanolamine

[0187] 1.9. Amides of β-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionicacid for example,

[0188]N,N′-di-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexamethylenediamine

[0189]N,N′-di-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-trimethylenediamine

[0190] N,N′-di-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hydrazine

[0191] 1.10 Diarylamines, for example, diphenylamine,N-phenyl-1-naphthylamine, N-(4-tert-octylphenyl)-1-naphthylamine,4,4′-di-tert-octyl-diphenylamine, reaction product ofN-phenylbenzylamine and 2,4,4-trimethylpentene, reaction product ofdiphenylamine and 2,4,4-trimethylpentene, reaction product ofN-phenyl-1-naphthylamine and 2,4,4-trimethylpentene.

[0192] 2. UV absorbers and light stabilizers

[0193] 2.1. 2-(2′-Hydroxyphenyl)-benzotriazoles, for example, the5′-methyl-, 3′,5′-di-tert-butyl-, 5′-tert-butyl-,5′-(1,1,3,3-tetramethylbutyl)-, 5-chloro-3′,5′-di-tert-butyl-,5-chloro-3′-tert-butyl-5′-methyl-, 3′-sec-butyl-5′-tert-butyl-,4′-octoxy, 3′,5′-di-tert-amyl-, 3′,5′-bis-(α,α-dimethylbenzyl),3′-tert-butyl-5′-(2-(omega-hydroxy-octa-(ethyleneoxy)carbonyl-ethyl)-,3′-dodecyl-5′-methyl-, and 3′-tert-butyl-5′-(2-octyloxycarbonyl)ethyl-,and dodecylated-5′-methyl derivatives.

[0194] 2.2. 2-Hydroxy-benzophenones, for example, the 4-hydroxy-,4-methoxy-, 4-octoxy, 4-decyloxy-, 4-dodecyloxy-, 4-benzyloxy,4,2′,4′-trihydroxy- and 2′-hydroxy-4,4′-dimethoxy derivatives.

[0195] 2.3. Esters of optionally substituted benzoic acids for example,phenyl salicylate, 4-tert-butylphenyl salicylate, octylphenylsalicylate, dibenzoylresorcinol, bis-(4-tert-butylbenzoyl)-resorcinol,benzoylresorcinol, 3,5-di-tert-butyl-4-hydroxybenzoic acid2,4-di-tert-butylphenyl ester and 3,5-di-tert-butyl-4-hydroxybenzoicacid hexadecyl ester.

[0196] 2.4. Acryates, for example, α-cyano-β,β-diphenylacrylic acidethyl ester or isooctyl ester, α-carbomethoxy-cinnamic acid methylester, α-cyano-β-methyl-p-methoxy-cinnamic acid methyl ester or butylester, α-carbomethoxy-p-methoxy-cinnamic acid methyl ester,N-(β-carbomethoxy-β-cyanovinyl)-2-methyl-indoline.

[0197] 2.5. Nickel compounds, for example, nickel complexes of2,2′-thio-bis-[4-(1,1,3,3-tetramethylbutyl)-phenol], such as the 1:1 or1:2 complex, optionally with additional ligands such as n-butylamine,triethanolamine or N-cyclohexyl-diethanolamine, nickeldibutyldithiocarbamate, nickel salts of4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid monoalkyl esters, suchas of the methyl, ethyl or butyl ester, nickel complexes of ketoximessuch as of 2-hydroxy-4-methyl-phenyl undecyl ketoxime, nickel complexesof 1-phenyl-4-lauroyl-5-hydroxy-pyrazole, optionally with additionalligands.

[0198] 2.6. Sterically hindered amines, for examplebis-(2,2,6,6-tetramnthylpiperidyl) sebacate,bis-(1,2,2,6,6-pentamethylpiperidyl) sebacate,n-butyl-3,5-di-tert.butyl-4-hydroxybenzyl malonic acidbis-(1,2,2,6,6-pentanemethylpiperidyl)ester, condensation product of1-hydroxyethyl-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinicacid, condensation product ofN,N′-(2,2,6,6-tetra-methylpiperidyl)-hexamethylenediamine and4-tert-octylamino-2,6-dichloro-s-triazine,tris-(2,2,6,6-tetramethylpiperidyl)-nitrilotriacetate,tetrakis-(2,2,6,6-tetramethyl-4-piperidyl)1,2,3,4-butanetetracarboxylate, 1,1′(1,2-ethanediyl)-bis-(3,3,5,5-tetramethylpiperazinone),bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate,1-(2-hydroxy-2-methylpropoxy)-4-octa-decanoyloxy-2,2,6,6-tetramethylpiperidine.

[0199] 2.7. Oxalic acid diamides, for example,4,4′-di-octyloxy-oxanilide,2,2′-di-octyloxy-5,5′-di-tert-butyl-oxanilide,2,2′-di-dodecyloxy-5,5′-di-tert-butyl-oxanilide,2-ethoxy-2′-ethyl-oxanilide, N,N′-bis (3-dimethylaminopropyl)-oxalamide,2-ethoxy-5-tert-butyl-2′-ethyloxanilide and its mixture with2-ethoxy-2′-ethyl-5,4′-di-tert-butyloxanilide and mixtures of ortho- andpara-methoxy- as well as of o- and p-ethoxy-disubstituted oxanilides.

[0200] 2.8. Hydroxyphenyl-s-triazines, for example2,6-bis-(2,4-dimethylphenyl)-4-(2-hydroxy-4-octyloxyphenyl)-s-triazine;2,6-bis-(2,4-dimethylphenyl)-4-(2,4-dihydroxyphenyl)-s-triazine;2,4-bis(2,4-dihydroxyphenyl)-6-(4-chlorophenyl)-s-triazine;2,4-bis[2-hydroxy-4-(2-hydroxyethoxy)phenyl]-6-(4-chlorophenyl)-s-triazine;2,4-bis[2-hydroxy-4-(2-hydroxy-4-(2-hydroxyethoxy)phenyl]-6-(2,4-dimethylphenyl)-s-triazine;2,4-bis[2-hydroxy-4-(2-hydroxyethoxy)-phenyl]-6-(4-bromophenyl)-s-triazine;2,4-bis[2-hydroxy-4-(2-acetoxyethoxy)phenyl]-6-(4-chlorophenyl)-s-triazine,2,4-bis(2,4-dihydroxyphenyl)-6-(2,4-dimethylphenyl)-s-triazine.

[0201] 3. Metal deactivators, for example, N,N′-diphenyloxalic aciddiamide, N-salicylal-N′-salicyloylhydrazine,N,N′-bis-salicyloylhydrazine,N,N′-bis-(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hydrazine,3-salicyloylamino-1,2,4-triazole, bis-benzylidene-oxalic aciddihydrazide.

[0202] 4. Phosphites and phosphonites, for example, triphenyl phosphite,diphenylalkyl phosphites, phenyldialkyl phosphites, tri-(nonylphenyl)phosphite, trilauryl phosphite, trioctadecyl phosphite,di-stearyl-pentaerythritol diphosphite, tris-(2,4-di-tert-butylphenyl)phosphite, di-isodecyl-pentaerythritol diphosphite,di-(2,4,6-tri-tert-butylphenyl)-pentaerythritol diphosphite,di-(2,4-di-tert-butyl-6-methylphenyl)-pentaerythritol diphosphite,di-(2,4-di-tert-butylphenyl)pentaerythritol diphosphite,tristearyl-sorbitol triphosphite, tetrakis-(2,4-di-tert-butylphenyl)4,4′-diphenylylenediphosphonite.

[0203] 5. Compounds which destroy peroxide, for example, esters ofβ-thiodipropionic acid, for example the lauryl, stearyl, myristyl ortridecyl esters, mercapto-benzimidazole or the zinc salt of2-mercaptobenzimidazole, zinc dibutyl-dithiocarbamate, dioctadecyldisulfide, pentaerydthitol tetrakis-(β-dodecylmercapto)-propionate.

[0204] 6. Hydroxylamines, for example, N,N-dibenzylhydroxylamine,N,N-diethylhydroxylamine, N,N-dioctylhydroxylamine,N,N-dilaurylhydroxylamine, N,N-ditetradecylhydroxylamine,N,N-dihexadecylhydroxylamine, N,N-dioctadecylhydroxylamine,N-hexadecyl-N-octadecyl-hydroxylamine,N-heptadecyl-N-octadecylhydroxylamine, N,N-dialkylhydroxylamine derivedfrom hydrogenated tallow amine.

[0205] 7. Nitrones, for example, N-benzyl-alpha-phenyl nitrone,N-ethyl-alpha-methyl nitrone, N-octyl-alpha-heptyl nitrone,N-lauryl-alpha-undecyl nitrone, N-tetradecyl-alpha-tridecyl nitrone,N-hexadecyl-alpha-pentadecyl nitrone,N-octadecyl-alpha-heptadecylnitrone, N-hexadecyl-alpha-heptadecylnitrone, N-octadecyl-alpha-pentadecyl nitrone,N-heptadecyl-alpha-heptadecyl nitrone, N-octadecyl-alpha-hexadecylnitrone, nitrone derived from N,N-dialkylhydroxylamine derived fromhydrogenated tallow amine.

[0206] 8. Polyamide stabilizers, for example copper salts in combinationwith iodides and/or phosphorus compounds and salts of divalentmanganese.

[0207] 9. Basic co-stabilizers, for example, melamine,polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, ureaderivatives, hydrazine derivatives, amines, polyamides, polyurethanes,alkali metal salts and alkaline earth metal salts of higher fatty acidsfor example Ca stearate, Zn stearate, Mg stearate, Na ricinoleate and Kpalmitate, antimony pyrocatecholate or zinc pyrocatecholate.

[0208] 10. Nucleating agents, for example, 4-tert-butyl-benzoic acid,adipic acid, diphenylacetic acid.

[0209] 11. Fillers and reinforcing agents, for example, calciumcarbonate, silicates, glass fibers, asbestos, talc, kaolin, mica, bariumsulfate, metal oxides and hydroxides, carbon black, graphite.

[0210] 12. Other additives, for example, plasticizers, lubricants,emulsifiers, pigments, optical brighteners, flameproofing agents,anti-static agents, blowing agents and thiosynergists such as dilaurylthiodipropionate or distearyl thiodipropionate.

[0211] 13. Benzofuranones and indolinones, for example those disclosedin U.S. Pat. No. 4,325,863, U.S. Pat. No. 4,338,244 or 5,175,312, or3-[4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butyl-benzo-furan-2-one,5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]benzofuran-2-one,3,3′-bis[5,7-di-tert-butyl-3-(4-[2-hydroxyethoxy]phenyl)benzofuran-2-one],5,7-di-tert-butyl-3-(4-ethoxyphenyl)-benzofuran-2-one,3-(4-acetoxy-3,5-dimethylphenyl)-5,7-di-tert-butyl-benzofuran-2-one,3-(3,5-di-methyl-4-pivaloyloxyphenyl)-5,7-di-tert-butyl-benzofuran-2-one.

[0212] The co-stabilizers, with the exception of the benzofuranoneslisted under 13, are added for example in concentrations of 0.01 to 10%,relative to the total weight of the material to be stabilized.

[0213] Further preferred compositions comprise, in addition tocomponents (a) and (b) further additives, in particular phenolicantioxidants, light stabilizers or processing stabilizers.

[0214] Particularly preferred additives are phenolic antioxidants (item1 of the list), sterically hindered amines (item 2.6 of the list),phosphites and phosphonites (item 4 of the list), UV absorbers (item 2of the list) and peroxide-destroying compounds (item 5 of the list).

[0215] Additional additives (stabilizers) which are also particularlypreferred are benzofuran-2-ones, such as described, for example, in U.S.Pat. Nos. 4,325,863, 4,338,244 or 5,175,312.

[0216] The phenolic antioxidant of particular interest is selected fromthe group consisting of n-octadecyl3,5-di-tert-butyl-4-hydroxyhydrocinnamate, neopentanetetrayltetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinammate), di-n-octadecyl3,5-di-tert-butyl-4-hydroxybenzylphosphonate,1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate,thiodiethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate),1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxy-benzyl)benzene,3,6-dioxaoctamethylenebis(3-methyl-5-tert-butyl-4-hydroxyhydrocinnamate),2,6-di-tert-butyl-p-cresol,2,2′-ethylidene-bis(4,6-di-tert-butylphenol),1,3,5-tris(2,6-dimethyl-4-tert-butyl-3-hydroxybenzyl)isocynurate,1,1,3,-tris(2-methyl-⁴-hydroxy-5-tert-butylphenyl)butane,1,3,5-tris[2-(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyloxy)ethyl]isocyanurate,3,5-di-(3,5-di-tert-butyl-4-hydroxybenzyl)mesitol, hexamethylenebis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate),1-(3,5-di-tert-butyl-4-hydroxyanilino)-3,5-di(octylthio)-s-triazine,N,N′-hexamethylene-bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamamide),calcium bis(ethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate),ethylene bis[3,3-di(3-tert-butyl-4-hydroxyphenyl)butyrate], octyl3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate,bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)hydrazide, andN,N′-bis[2-(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyloxy)-ethyl]-oxamide.

[0217] A most preferred phenolic antioxidant is neopentanetetrayltetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), n-octadecyl3,5-di-tert-butyl-4-hydroxyhydrocinnamate,1,3,5-tri-methyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene,1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate,2,6-di-tert-butyl-p-cresol or2,2′-ethylidene-bis(4,6-di-tert-butylphenol).

[0218] The hindered amine compound of particular interest is selectedfrom the group consisting of

[0219] bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate,

[0220] bis(1,2,2,6,6-pentamethylpiperidin-4-yl) sebacate,

[0221] di(1,2,2,6,6-pentamethylpiperidin-4-yl)(3,5-di-tert-butyl-4-hydroxybenzyl)butylmalonate,

[0222] 4-benzoyl-2,2,6,6-tetramethylpiperidine,4-stearyloxy-2,2,6,6-tetramethylpiperidine,

[0223]3-n-ctyl-7,7,9,9-tetramethyl-1,3,8-triaza-spiro[4.5]decane-2,4-dione,

[0224] tris(2,2,6,6-tetramethylpiperidin-4-yl) nitrilotriacetate,

[0225] 1,2-bis(2,2,6,6-tetramethyl-3-oxopiperazin-4-yl)ethane,2,2,4,4-tetramethyl-7-oxa-3,20-diaza-21-oxodispiro[5.1.11.2]heneicosane, polycondensation product of2,4-dichloro-6-tert-octylamino-s-triazine and4,4′-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine),polycondensation product of1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinicacid, polycondensation product of4,4′-hexamethylenebis-(amino-2,2,6,6-tetra-methylpiperidine) and1,2-dibromoethane,

[0226] tetrakis(2,2,6,6-tetramethylpiperidin-4-yl)1,2,3,4-butanetetracarboxylate,

[0227] tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl)1,2,3,4-butanetetracarboxylate,

[0228] polycondensation product of 2,4-dichloro-6-morpholino-s-triazineand

[0229] 4,4′-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine),N,N′,N″,N′″-tetrakis[(4,6-bis(butyl-1,2,2,6,6-pentamethyl-piperidin-4-yl)-amino-s-triazin-2-yl]-1,10-diamino-4,7-diazadecane,mixed[2,2,6,6-tetramethylpiperidin-4-yl/β,β,β′,β′-tetramethyl-3,9-(2,4,8,10-tetraoxaspiro[5.5]-undecane) diethyl] 1,2,3,4-butanetetracarboxylate,mixed [1,2,2,6,6-pentamethylpiperidin-4-yl/β,β,β′,β′-tetramethyl-3,9-(2,4,8,10-tetraoxaspiro[5.5]-undecane)diethyl]1,2,3,4-butanetetracarboxylate, octamethylenebis(2,2,6,6-tetramethyl-piperidin-4-carboxylate),

[0230] 4,4′-ethylenebis(2,2,6,6-tetramethylpiperazin-3-one),N-2,2,6,6-tetramethyl-piperidin-4-yl-n-dodecylsuccinimide,N-1,2,2,6,6-pentamethyl-piperidin-4-yl-n-dodecylsuccinimide,N-1-acetyl-2,2,6,6-tetramethylpiperidin-4-yln-dodecylsuccinimide,1-acetyl3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione,di-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate,di-(1-cyclohexyloxy-2,2,6,6-tetra-methylpiperidin4-yl) succinate,1-octyloxy-2,2,6,6-tetramethyl-4-hydroxy-piperidine,poly-{[6-tert-octylamino-s-triazin-2,4-diyl][2-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)imino-hexamethylene-[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)imino],2,4,6-tris[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-s-triazine,bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl)]sebacate; a mixture ofbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate andbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]adipate;1-(2-hydroxy-2-methyl-propoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine;bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]adipate;bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethyl-piperidin-4-yl]glutarate;bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin4-yl]succinate; a mixture ofbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate andbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]succinate;1-(4-octadecanoyloxy-2,2,6,6-tetramethylpiperidin-1-yloxy)-2-octadecanoyloxy-2-methylpropane;1-(2-hydroxy-2-methylpropoxy)-4-[9-(methoxy-carbonyl)nonanoyloxy]-2,2,6,6-tetramethyl-piperidine;1-(2-hydroxy-2-methylpropoxy)-4-[5-(methoxy-carbonyl)pentanoyloxy]-2,2,6,6-tetra-methylpiperidine;1-(2-hydroxy-2-methylpropoxy)-4-[3-(methoxy-carbonyl)propionyloxy]-2,2,6,6-tetramethylpiperidine;1-(2-hydroxy-2-methylpropoxy)-4-[4-(methoxy-carbonyl)-butyryloxy]-2,2,6,6-tetramethylpiperidine;condensation product of4-hydroxy-1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidinewith hexamethylene diisocyanate and terminated with methoxy;condensation product of4-hydroxy-1-(2-hydroxy-ethoxy)-2,2,6,6-tetramethyl-piperidine withhexamethylene diisocyanate and terminated with methoxy; and thecondensation product of4-hydroxy-1-(2-hydroxy-1-phenethoxy)-2,2,6,6-tetramethylpiperidine withhexamethylene diisocyanate and terminated with methoxy.

[0231] A most preferred hindered amine compound isbis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate,bis(1,2,2,6,6-pentamethylpiperidin-4-yl) sebacate,di(1,2,2,6,6-pentamethylpiperidin-4-yl)(3,5-di-tert-butyl-4-hydroxybenzyl)butylmalonate, the polycondensationproduct of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidineand succinic acid, the polycondensation product of2,4-dichloro-6-tert-octylamino-s-triazine and4,4′-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine),N,N′,N″,N′″-tetrakis[(4,6-bis(butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino)-s-triazine-2-yl]-1,10-diamino-4,7-diazadecane.di-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate,di-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate,1-octyloxy-2,2,6,6-tetramethyl-4-hydroxy-piperidine,poly-{[6-tert-octylamino-s-triazin-2,4-diyl][2-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)imino-hexamethylene-[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)imino],2,4,6-tris[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-n-butylamino]-s-triazine,or1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine.

[0232] The instant composition can additionally contain another UVabsorber selected from the group consisting of the benzotriazoles, thes-triazines, the oxanilides, the salicylates, the hydroxybenzophenones,the benzoates and the α-cyanoacrylates.

[0233] Particularly, the instant composition may additionally contain aneffective stabilizing amount of at least one other2-hydroxyphenyl-2H-benzotriazole; another tris-aryl-s-triazine; orhindered amine or mixtures thereof.

[0234] Preferably, the 2-hydroxyphenyl-2H-benzotriazole is selected fromthe group consisting of2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole;

[0235] 2-[2-hydroxy-3,5-di(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole;

[0236]2-[2-hydroxy-3-(α,α-dimethylbenzyl)-5-tert-octylphenyl]-2H-benzotriazole;

[0237]2-{2-hydroxy-3-tert-butyl-5-[2-(omega-hydroxy-octa(ethyleneoxy)carbonyl)ethyl]-phenyl}-2H-benzotriazole;

[0238] 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;

[0239]5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole;

[0240] 2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole; and

[0241]2-{2-hydroxy-3-tert-butyl-5-[2-(octyloxy)carbonyl)ethyl]phenyl}-2H-benzo-triazole.

[0242] Preferably, the other tris-aryl-s-triazine is selected from thegroup consisting of

[0243]2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine;

[0244] 2,4-diphenyl-6-(2-hydroxy-4-hexyloxyphenyl)-s-triazine;

[0245]2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-do-/t-decyloxy-2-hydroxypropoxy)-phenyl]-s-triazine;

[0246]2,4-bis(2,4-dimethylphenyl)-6-[2-hydroxy-4-(3-nonyloxy*-2-hydroxy-propyloxy)-5-α-cumylphenyl]-s-triazine.(* denotes a mixture of octyloxy, nonyloxy and decyloxy groups.), and

[0247]2,4-bis(biphenylyl)-6-[2-hydroxy-4-(3-nonyloxy*-2-hydroxypropyloxy)phenyl]-s-triazine.(* denotes a mixture of octyloxy, nonyloxy and decyloxy groups.)

[0248] The instant compounds are often used in conjunction with one ormore coadditive stabilizers where the coadditive stabilizer is ahindered phenolic antioxidant selected from the group consisting ofneopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamate,octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate,1,3,5-trimethyl-2,4,6-tris(3,5,-di-tert-butyl-4-hydroxybenzyl)benzene,1,2-bis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamoyl)hydrazine, calcium[bis(monoethyl 3,5-ditert-butyl-4-hydroxybenzyl)-phosphonate],1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate and1,3,5-tris(3-hydroxy-4-tert-butyl-2,6-dimethylbenzyl) isocyanurate; oris an organophosphorus stabilizer selected from the group consisting oftris(2,4-di-tert-butylphenyl) phosphite,bis(2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite,2,2′,2″-nitrilo[triethyl-tris-(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite], tetrakis(2,4-di-butylphenyl) 4,4′-biphenylenediphosphonite,tris(nonylphenyl) phosphite, bis(2,4-di-tert-butylphenyl)pentaerythrityl diphosphite, 2,2′-ethylidenebis(2,4-di-tert-butylphenyl)fluorophosphite and 2-butyl-2-ethylpropan-1,3-diyl2,4,6-tri-tert-butylphenyl phosphite; or is5,7-di-tert-butyl-3-(3,4-dimethylphenyl)-2H-benzofuran-2-one; or isN,N-dialkylhydroxyl-amine made by the direct oxidation ofN,N-di(hydrogenated tallow)amine; or is a hindered amine selected fromthe group consisting of bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate,the polycondensation product of1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinicacid,N,N′,N″,N′″-tetrakis[4,6-bis(butyl-1,2,2,6,6-penta-methylpiperidin-4-yl)amino-s-triazin-2-yl]-1,10-diamino-4,7-diazadecane,the polycondensation product of4,4′-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and2,4-dichloro-6-tert-octylamino-s-triazine, the polycondensation productof 4,4′-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and2,4-dichloro-6-morpholino-s-triazine, the polycondensation product of4,4′-hexamethylenebis(amino-1,2,2,6,6-pentamethylpiperidine) and2,4-dichloro-6-morpholino-s-triazine, 2,2,6,6-tetramethylpiperidin-4-yloctadecanoate,3-dodecyl-1-(1-acetyl-2,2,6,6-tetramethylpiperidin-4-yl)-pyrrolidin-2,5-dione,1,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino)-s-triazine,poly[methyl 3-(2,2,6,6-tetramethylpiperidin-4-yloxy)-propyl]siloxane,the polycondensation product of2,4-dichloro-6-(2,2,6,6-tetramethyl--piperidin-4-yl)butylamino)-s-triazine,2,2′ethylene-bis([2,4-(2,2,6,6-tetramethyl-piperidin-4-yl)butylamino-s-triazin-6-yl]aminotrimethyleneamino},oligomer ofN—{[2-(N-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamineterminated with 2,4-bis(dibutylamino)-s-triazin-6-yl, N,N′,N″-tris{2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine,N,N′,N′″-tris{2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine and N,N′,N″,N′″-tetrakis{2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine;or is another N-hydrocarbyloxy substituted hindered amines selected fromthe group consisting ofbis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate,bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) adipate,bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) adipate,bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate,1-cyclohexyloxy-2,2,6,6-tetra-methylpiperidin-4-yl octadecanoate,N,N′,N″-tris{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine,N,N′,N′″-tris2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butyl-amino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine andN,N′,N″,N′″-tetrakis(2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-6-yl)-3,3′-ethylenediiminodipropylamine;or a hydroxy substituted N-hydrocarbyloxy substituted hindered amineselected from the group consisting ofbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl)]sebacate; a mixture ofbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate andbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]adipate;1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine;bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]adipate;bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate;bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]succinate; a mixture ofbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate andbis-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]succinate;1-(4-octadecanoyloxy-2,2,6,6-tetramethylpiperidin-1-yloxy)-2-octadecanoyl-oxy-2-methylpropane;1-(2-hydroxy-2-methylpropoxy)-4-[9-(methoxy-carbonyl)-nonanoyloxy]-2,2,6,6-tetramethylpiperidine;1-(2-hydroxy-2-methylpropoxy)-4-[5-(methoxy-carbonyl)pentanoyloxy]-2,2,6,6-tetramethylpiperidine;1-(2-hydroxy-2-methylpropoxy)-4-[3-(methoxy-carbonyl)propionyloxy]-2,2,6,6-tetramethylpiperidine;1-(2-hydroxy-2-methylpropoxy)-4-[4-(methoxy-carbonyl)butyryloxy]-2,2,6,6-tetramethyl-piperidine;or is a UV absorber selected from the group consisting of2-(2-hydroxy-3,5-di-α-cumylphenyl)-2H-benzotriazole,2-(2-hydroxy-5-methylphenyl)-2H-benzo-triazole,5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole,2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole,2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole,2,4-di-tert-butylphenyl 3,5-di-tert-butyl4-hydroxybenzoate,2-hydroxy-4-n-octyloxybenzophenone,2,4-bis(2,4-dimethyphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine,oligomer ofN-{2-[(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′-bis(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamineterminated with 2,4-bis(dibutylamino)-s-triazin-6-yl, the condensationproduct of 2-morpholino-4,6-dichloro-s-triazine withN,N′-bis(1,2,2,6,6-pentamethyl-piperidin-4-yl)-1,6-hexanediamine; ormixtures thereof.

[0249] Preferably the coadditive stabilizer is neopentanetetrayltetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate,tris(2,4-di-tert-butylphenyl) phosphite, N,N-dialkylhydroxylamine madeby the direct oxidation of N,N-di(hydrogenated tallow)amine,N,N′,N″,N′″-tetrakis[4,6-bis(butyl-1,2,2,6,6-pentamethylpiperidin-4-yl)amino-s-triazin-2-yl]-1,10-diamino-4,7-diazadecane,the polycondensation product of4,4′-hexamethylene-bis(amino-2,2,6,6-tetramethylpiperidine) and2,4-dichloro-6-tert-octylamino-s-triazine, the polycondensation productof 4,4′-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and2,4-dichloro-6-morpholino-s-triazine, the polycondensation product of4,4′-hexamethylenebis(amino-1,2,2,6,6-pentamethylpiperidine) and2,4-dichloro-6-morpholino-s-triazine, oligomer ofN-{[2-(N-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamineterminated with 2,4-bis(dibutylamino)-s-triazin-6-yl, N,N′,N″-tris{2,4-bis[N-(1,2,2,6,6-pentamethyl-piperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine,N,N′,N′″-tris{2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamineand N,N′,N″,N′″-tetrakis{2,4-bis[N-(1,2,2,6,6-penta-methylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine,oligomer ofN-{2-[(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′-bis(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamineterminated with 2,4-bis(dibutylamino)-s-triazin-6-yl, or thecondensation product of 2-morpholino-4,6-dichloro-s-triazine withN,N′-bis(1,2,2,6,6-pentamethylpiperidin-4-yl)-1,6-hexanediamine.

[0250] The alkyd resin lacquers which can be stabilized against theaction of light and moisture in accordance with the instant inventionare the conventional stoving lacquers which are used in particular forcoating automobiles (automobile finishing lacquers), for examplelacquers based on alkyd/melamine resins and alkyd/acrylic/melamineresins (see H. Wagner and H. F. Sarx, “Lackkunstharze” (1977), pages99-123). Other crosslinking agents include glycouril resins, blockedisocyanates or epoxy resins.

[0251] The lacquers stabilized in accordance with the invention aresuitable both for metal finish coatings and solid shade finishes,especially in the case of retouching finishes, as well as various coilcoating applications. The lacquers stabilized in accordance with theinvention are preferably applied in the conventional manner by twomethods, either by the single-coat method or by the two-coat method. Inthe latter method, the pigment-containing base coat is applied first andthen a covering coat of clear lacquer over it.

[0252] It is also to be noted that the compounds of the presentinvention are applicable for use in non-acid catalyzed thermoset resinssuch as epoxy, epoxy-polyester, vinyl, alkyd, acrylic and polyesterresins, optionally modified with silicon, isocyanates or isocyanurates.The epoxy and epoxy-polyester resins are crosslinked with conventionalcrosslinkers such as acids, acid anhydrides, amines and the like.Correspondingly, the epoxide may be utilized as the crosslinking agentfor various acrylic or polyester resin systems that have been modifiedby the presence of reactive groups on the backbone structure.

[0253] When used in two-coat finishes, the compounds of the instantinvention can be incorporated in the clear coat or both in the clearcoat and in the pigmented base coat.

[0254] When water-soluble, water miscible or water dispersible coatingare desired ammonium salts of acid groups present in the resin areformed. Powder coating composition can be prepared by reacting glycidylmethacrylate with selected alcohol components.

[0255] The instant benzotriazoles are made by conventional methods forpreparing such compounds. The usual procedure involves the diazotizationof a substituted o-nitroaniline followed by coupling the resultantdiazonium salt with a substituted phenol and reduction of the azobenzeneintermediate to the corresponding desired benzotriazole. The startingmaterials for these benzotriazoles are largely items of commerce or canbe prepared by normal methods of organic synthesis.

[0256] While the instant benzotriazoles with their enhanced durabilityare particularly suited for automotive coating applications, it iscontemplated that they will also be espeically useful in otherapplications where their enhanced durability is required such as insolar films and the like.

[0257] The following examples are for illustrative purposes only and arenot to be construed to limit the scope of the instant invention in anymanner whatsoever.

EXAMPLE 1 2-(1, 1-Diphenylethyl)-4-tert-butylphenol

[0258] To a 500 mL three-necked flask equipped with a mechanicalstirrer, 40 g of 4-tert-butylphenol, 40 g of hexanes and 1.9 g ofp-toluenesulfonic acid are charged. The slurry is heated to 60° C. atwhich time 62 g of 1,1-diphenylethylene is added. The temperature isincreased to 110° C. and the hexanes are removed by distillation. After4.5 hours, the reaction mass is cooled to ambient temperature andpurified by silica gel chromatography using heptane/ethyl acetate as theeluent. Sixty (60) grams of the title compound is obtained whosestructure is confined by ¹H nmr.

EXAMPLE 2 2-Nitrophenyldiazonium Chloride

[0259] To a 500 mL three-necked flask equipped with a mechanical stirrerare added 60 g of 2-nitroaniline and 134.2 g of concentratedhydrochloric acid. After heating to 65° C., 46 g of water is added afterwhich the reactor is cooled to 0° C. Sodium nitrite (74.2 g, 40% aqueoussolution) is slowly added to the slurry while maintaining a temperatureof 0° C. The diazonium salt solution is filtered to give 290 g ofsolution which is stored at −15° C. for later use.

EXAMPLE 32-Nitro-2′-hydroxy-3′-(1,1-diphenylethyl)-5′-tert-butylmonoazobenzene

[0260] To a 500 mL three-necked flask fitted with a mechanical stirrerare added 26.6 g of 2-(1,1-diphenylethyl)-4-tert-butylphenol, preparedin Example 1, 140 g of methanol, 17.5 g of sodium hydroxide pellets, 4 gof toluene and 5 g of water. This solution is cooled to −15° C. and 75 gof the diazonium salt solution, prepared in Example 2, is added slowlyover three hours. The crimson slurry is acidified to a pH of 2 withdilute hydrochloric acid. The monoazo compound formed is filtered andwashed with water. The crude cake is over dried to yield 37.7 g ofcrimson red solid which contains some residual sodium chloride. Thiscrude product with is the title compound melts at 157-160° C. and itsstructure is verified by ¹H nmr and mass spectroscopy.

EXAMPLE 42-[2-Hydroxy-3-(1,1-diphenylethyl)-5-tert-butyl-phenyl]-2H-benzotriazoleN-Oxide

[0261] To a 500 mL three-necked flask equipped with a mechanical stirrerare charged 25 g of the crude monoazo compound prepared in Example 3, 50g of toluene, 0.5 g of 5% palladium on carbon catalyst, and 100 g ofn-butylamine. This solution is cooled to 5° C. and hydrazine (3 g) isadded slowly over two hours while not allowing the temperature to riseabove 20° C. The catalyst is removed by filtration and the solvent isdistilled under vacuum. The benzotriazole N-oxide compound is thencrystallized from methanol/toluene. After vacuum drying, 16.1 g of thedesired title compound is obtained as an orange solid melting at201-203° C. The structure is confirmed by ¹H nmr and mass spectroscopy.

EXAMPLE 52-[2-Hydroxy-3-(1,1-diphenylethyl)-5-tert-butylphenyl]-2H-benzotriazole

[0262] To a 500 mL three-necked flask fitted with a mechanical stirrer,3 g of sodium hydroxide pellets and 50 mL of 2-butanol are charged andheated to 82° C. To this solution, a slurry of 200 mL of 2-butanone, 15g of the benzotriazole N-oxide prepared in Example 4, and 0.67 g of2,3-dichloro-1,4-naphthoquinone is added over 40 minutes. The mixture isrefluxed at 88° C. for five hours while distilling off 2-butanone.Additional 2-butanol (50 mL) is added to replace what is lost duringdistillation of the 2-butanone. After cooling the reaction mixture toambient temperature, 25 g of water and 30 mL of ethyl acetate are addedat which time the pH is reduced to 2 with 30% aqueous sulfuric acid.After splitting off the aqueous layer, the solvent is removed bydistillation and the crude solid purified by silica gel chromatographyusing heptane/ethyl acetate as the eluent. After collecting the desiredfractions and crystallization from methanol/toluene, 14 g of the titlecompound is obtained after drying as a light yellow solid melting at172-173° C. The structure is confirmed by ¹H nmr and mass spectroscopy.

EXAMPLE 6 4-Chloro-2-nitrophenyldiazonium Chloride

[0263] The title diazonium salt solution is prepared according to theprocedure of Example 2 where 60 g of 4-chloro-2-nitroaniline are used toprepared 281.3 g of a 23% aqueous solution of the title compound whichis stored at −15° C. till use.

EXAMPLE 74-Chloro-2-nitro-2′-hydroxy-3′-(1,1-diphenylethyl)-5′-tert-butylmonoazobenzene

[0264] The title compound is prepared according to the method of Example3 from 30 g of the phenol prepared in Example 1 and 113 g of 23% aqueousdiazonium salt solution prepared in Example 6. A crimson red solid isobtained whose structure is consistent with the tide compound by ¹H nmrand mass spectroscopy.

EXAMPLE 85-Chloro-2-[2-hydroxy-3-(1,1-diphenylethyl)-5-tert-butylphenyl]-2H-benzotriazoleN-Oxide

[0265] The title compound is prepared according to the method of Example4 where 30 g of the monoazo compound of Example 7 is used to prepare 15g of the title compound as an orange solid melting at 148-154° C. whosestructure is consistent with analysis by ¹H nmr and mass spectroscopy.

EXAMPLE 95-Chloro-2-[2-hydroxy-3-(1,1-diphenylethyl)-5-tert-butylphenyl]-2H-benzotriazole

[0266] The title compound is prepared according to the method of Example5 from 12.25 g of the benzotriazole N-oxide prepared in Example 8. Thetitle compound is obtained as 8 g of a light yellow solid melting at177-178° C. The structure is confirmed by analysis by ¹H nmr and massspectroscopy.

EXAMPLE 10 2-(1, 1-Diphenylethyl)-4-tert-octylphenol

[0267] The title compound is prepared according to the procedure ofExample 1 from 41 g of 4-tert-octylphenol. The desired compound isobtained in a yield of 15.5 g whose structure is verified by ¹H nmr.

EXAMPLE 11 4-Trifluoromethyl-2-nitrophenyldiazonium Bisulfate

[0268] To a 500 mL three-necked flask equipped with a mechanical stirreris added 99.5 g of concentrated sulfuric acid and 62.5 g of4-trifluoro-2-nitroaniline (or 4-amino-3-nitro-benzotrifluoride). Afterheating to 75° C., 200 g of water is added at which time the temperatureis reduced to 0° C. Sodium nitrite solution (52.9 g, 40% by weight inwater) is added over two hours while maintaining the temperature at 0-5°C. The title diazonium salt solution (351 g) is filtered and stored at−15° C. for later use.

EXAMPLE 124-Trifluoromethyl-2-nitro-2′-hydroxy-3′-(1,1-diphenylethyl)-5′-tert-octylmonoazobenzene

[0269] To a 500 mL three-necked flask fitted with a mechanical stirreris added 35.1 g of the phenol prepared in Example 10, 80 g of xylenesand 1.7 g of PETROSUL® M-60 (surfactant made by Penreco). At ambienttemperature, the diazonium salt solution prepared in Example 11 ischarged over five hours. Xylenes (200 g) and 82 g of 25% aqueous sodiumhydroxide solution are charged at the conclusion of the diazonium saltaddition. The aqueous layer is removed and xylene is distilled off undervacuum. The title compound is obtained in a yield of 72 g as a crudecrimson oil.

EXAMPLE 135-Trifluoromethyl-2-[2-hydroxy-3-(1,1-diphenylethyl)-5-tert-octylphenyl]-2H-benzotriazoleN-Oxide

[0270] The desired benzotriazole N-oxide compound is prepared accordingto the procedure of Example 4. The monoazo compound of Example 12 (72 g)is reduced to give the title compound as orange crystals melting at143-145° C. The structure is consistent as analyzed by ¹H nmr and massspectroscopy.

EXAMPLE 145-Trifluoromethyl-2-[2-hydroxy-3-(1,1-diphenylethyl)-5-tert-octylphenyl]-2H-benzotriazole

[0271] The desired compound is prepared according to the method ofExample 5 from 20.1 g of the corresponding benzotriazole N-oxideprepared in Example 13. The title compound is obtained in a yield of18.8 g as a light yellow solid melting at 66-77° C. The structure of thecompound is consistent by ¹H nmr and mass spectroscopy.

EXAMPLE 15 Polycarbonate

[0272] The durability of representative instant benzotriazoles inthermoplastic substrates is determined by incorporating various testcompounds into solvent cast films of polycarbonate resins. The freestanding films are mounted into cardboard holders, secured in metalframes and exposed in an Atlas C165 Xenon-arc Weather-Ometer under dryconditions according to ASTM G26. Loss of UV absorber is determined bymonitoring the loss of diagnostic UV absorption.

[0273] Polycarbonate flake (LEXAN® 145, General Electric) is dissolvedin methylene chloride at room temperature along with between 1 and 3% byweight of test benzotriazole, based on the polycarbonate. Films are castusing a calibrated drawdown bar to prepare 1 mil thick film afterdrying. Compound of Change in Initial Example* (% by weight) Absorbanceafter 1500 hours TINUVIN ® 329 (1.81%) 0.14 TINUVIN ® 234 (2.50%) 0.14Example 5 (2.50%) 0.10

[0274] These data show that the instant compounds are particularlyefficacious when used in thermoplastic compositions, such aspolycarbonate, even surpassing a commercial UV absorber ineffectiveness. This is shown by the reduction in absorbance loss afterexposure to actinic radiation.

EXAMPLE 16 Polycarbonate

[0275] Polycarbonate films of about 1 mil thickness and containing a UVabsorber are prepared by dissolving polycarbonate granules (LEXAN® 145,General Electric) and UV absorbers in methylene chloride and casting thefilms on a glass plate using a drawdown bar. The films are exposed for750 hours in a Xenon Arc Weather-Ometer according to ASTM G26 testmethod and the color change (ΔYI) versus that for unexposed films arerecorded below. The color measurements (yellowness index−YI) are carriedout on an ACS spectrophotometer, small area view, spectral componentincluded d/8, D65, 10° observer, YI 1925 for unexposed and exposedsamples after 1000 hours. Compound of Example* (% by weight) ΔYI Blank(no stabilizer) 17.82 TINUVIN ® 234 (2.50%) 5.56 Example 5 (2.50%) 5.52

[0276] These data show that the instant compounds are particularlyefficacious when used in thermoplastic compositions, such aspolycarbonate, comparable to a commerical UV absorber in effectiveness.This is shown by the reduction of yellowing (ΔYI) after exposure toactinic radiation.

EXAMPLE 17 Poly(methyl methacrylate)

[0277] The durability of representative instant benzotriazoles inthermoplastic substrates is determined by incorporating various testcompounds into solvent cast films of a poly(methyl methacrylate) (PMMA)resin. The free standing films are mounted into cardboard holders,secured in metal frames and exposed in an Atlas C165 Xenon-arcWeather-Ometer under dry conditions according to ASTM G26. Loss of UVabsorber is determined by monitoring the loss of diagnostic UVabsorption as described earlier. Performance is measured by a change incolor or the physical integrity of the film, or in loss of absorbance ofthe UV absorber at λmax.

[0278] Poly(methyl methacrylate), medium molecular weight, Aldrich, isdissolved in methylene chloride at room temperature along with between 1and 3% by weight of test benzotriazole, based on the PMMA resin. Filmsare cast using a calibrated drawdown bar to prepare 1 mil thick filmafter drying. Compound of Change in Initial Example* (% by weight)Absorbance after 1500 hours TINUVIN ® 328 (1.96%) 0.31 TINUVIN ® 234(2.50%) 0.14 Example 9 (2.69%) 0.09 Example 14 (3.19%) 0.06

[0279] These data show that the instant compounds are particularlyefficacious when used in thermoplastic compositions, such as poly(methylmethacrylate), even surpassing two commercial UV absorbers ineffectiveness. This is shown by the reduction in absorbance loss afterexposure to actinic radiation.

EXAMPLE 18 Incorporation into Photographic Layers

[0280] A gelatin coat of the following composition (per m²) is appliedin the customary manner to a polyester base. Components Amount Gelatin1200 mg  Tricresyl Phosphate 510 mg Hardener*  40 mg Wetting Agent** 100mg Test UV Absorber 400 mg

[0281] The gelatin coats are dried at 20° C. for seven days.

[0282] When the instant UV absorbers are used, clear transparent coatsare obtained which are suitable for photographic recording material forexample as a UV filter coat. % Change in Initial Optical Density (2.0)after Test Compound 60 KJ Exposure 120 KJ Exposure TINUVIN ® 328 9.734.3 Example 14 1 1

[0283] These data show that the instant compounds when used in aphotographic layer are extremely photostable.

EXAMPLE 19 Photographic Compositions

[0284] A polyethylene-coated base material is coated with a gelatin coatcomprising silver bromide and a magenta coupler (M-9). The gelatin coatincludes the following component (per m² of base material): ComponentAgBr coat Gelatin 5.15 g Hardener*  300 mg Wetting Agent**   85 mgSilver Bromide  260 mg Magenta Coupler(M-9)  325 mg Tricresyl Phosphate 162 mg

[0285] A step wedge having a density difference of 0.3 log E per step isexposed onto each of the resulting samples which are then processed inaccordance with the manufacturer's instructions in the P94 process ofAgfa Gevaert for negative color papers.

[0286] After exposure and processing, the density of reflectance in thegreen region for the magenta stage is measured at a density of between0.9 and 1.1 of the wedge.

[0287] A UV absorber filter comprising an instant test benzotriazole isprepared on transparent base material as described in Example 18.

[0288] The wedge is subsequently exposed behind the UV absorber filterin an Atlas exposure instrument at 15 kJ/cm² and the reflectance densityis measured again. The magenta dye density loss (−ΔD) is greatly reducedby the instant test compound as stabilizer in comparison with the samplecontaining no stabilizer.

EXAMPLE 20 Photographic Compositions

[0289] The procedure described in Example 18 is repeated using a mixtureof 2 parts by weight of an instant test compound and 1 part by weight ofan s-triazine UV absorber. Clear transparent coats are obtained whichare suitable for a photographic recording material.

EXAMPLE 21 Photographic Compositions

[0290] A photographic material having the following layer structure isprepared:

[0291] top layer

[0292] red-sensitive layer

[0293] second gelatin layer

[0294] green-sensitive layer

[0295] first gelatin layer

[0296] blue-sensitive layer

[0297] polyethylene base

[0298] The gelatin layers consist of the following components (per m² ofbase material):

[0299] Blue-Sensitive Layer

[0300]α-(3-benzyl-4-ethoxyhydantoin-1-yl)-a-pivaloyl-2-chloro-5-[α-(2,4-di-tert-amylphenoxy)-acetanilide(400 mg)

[0301]α-(1-butylphenylurazol-4-yl)-α-pivaloyl-5-(3-dodecanesulfonyl-2-methylpropanamido)-2-methoxyacetamide(400 mg)

[0302] dibutyl phthalate (130 mg)

[0303] dinonyl phthalate (130 mg)

[0304] gelatin (1200 mg)

[0305]1,5-dioxa-3-ethyl-3-[β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionytloxymethyl]-8,10-diphenyl-9-thia[5.5]spiroundecane (150 mg)

[0306] bis(1-acryloyl-2,2,6,6-tetramethyl-4-piperidyl)2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)-malonate (150 mg)

[0307] 3,5-di-tert-butyl-4-hydroxy(2,4-di-tert-amylphenyl)benzoate (150mg)

[0308] poly(N-tert-butylacrylamide) (50 mg)

[0309] blue-sensitive silver chlorobromide emulsion (240 mg)

[0310] First Gelatin Interlayer

[0311] gelatin (1000 mg)

[0312] 2,5-di-tert-octylhydroquinone (100 mg)

[0313] hexyl5-[2,5-dihydroxy-4-(4-hexyloxycarbonyl-1,1-dimethylbutyl)phenyl]-5-methyl-hexanoate(100 mg)

[0314] dibutyl phthalate (200 mg)

[0315] diisobutyl phthalate (200 mg)

[0316] Green-Sensitive Layer

[0317]7-chloro-2-{2-[2-(2,4-di-tert-amylphenoxy)octanamido]-1-methylethyl}-6-methyl-1H-pyrazolo[1,5b][1,2,4]triazole(100 mg)

[0318]6-tert-butyl-7-chloro-3-(3-dodecanesulfonylpropyl)-1H-pyrazolo)-1H-pyrazolo[5,1-o][1,2,4]triazole(100 mg)

[0319] dibutyl phthalate (100 mg)

[0320] dicresyl phosphate (100 mg)

[0321] trioctyl phosphate (100 mg)

[0322] gelatin (1400 mg)

[0323] 3,3,3′,3′-tetramethyl-5,5′,6,6′-tetrapropoxy-1,1′-spirobiindane(100 mg)

[0324] 4-(isotridecyloxyphenyl)thiomorpholine-1,1-dioxide (100 mg)

[0325] 4,4′-butylidenebis(3-methyl-6-tert-butylphenol) (50 mg)

[0326] 2,2′-isobutylidenebis(4,6-dimethylphenol) (10 mg)

[0327] 3,5-dichloro-4-(hexadecyloxycarbpnyloxy)ethylbenzoate (20 mg)

[0328] 3,5-bis[3-(2,4-di-tert-amylphenoxy)propylcarbamoyl] sodiumbenzenesulfinate (20 mg)

[0329] green-sensitive silver chlorobromide emulsion (150 mg)

[0330] Second Gelatin Interlayer

[0331] gelatin (1000 mg)

[0332]5-chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)benzo-1,2,3-triazole (200mg)

[0333] 2-(3-dodecyl-2-hydroxy-5-methylphenyl)benzo-1,2,3-triazole (200mg)

[0334] trinonyl phosphate (300 mg)

[0335] 2,5-di-tert-octylhydroquinone (50 mg)

[0336] hexyl5-[2,5-dihydroxy-4-(4-hexyloxycarbonyl-1,1-dimethylbutyl)phenyl]-5-methylhexanoate(50 mg)

[0337] Red-Sensitive Layer

[0338]2-[α-(2,4-di-tert-amylphenoxy)butanamido]-4,6-dichloro-5-ethylphenol(150 mg)

[0339] 2,4-dichloro-3-ethyl-6-hexadecanamidophenol (150 mg)

[0340]4-chloro-2-(1,2,3,4,5-pentafluorobenzamido)-5-[2-(2,4-di-tert-amylphenoxy)-3-methyl-butanamido]phenol(100 mg)

[0341] dioctyl phthalate (100 mg)

[0342] dicyclohexyl phthalate (100 mg)

[0343] gelatin (1200 mg)

[0344]5-chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)benzo-1,2,3-triazole (100mg)

[0345] 2-(3-dodecyl-2-hydroxy-5-methylphenyl)benzo-1,2,3-triazole (100mg)

[0346] 3,5-di-tert-butyl-4-hydroxy(2,4-di-tert-amylphenyl)benzoate (50mg) poly(N-tert-butylacrylamide) (300 mg)

[0347] N,N-diethyl-2,4-di-tert-amylphenoxyacetamide (100 mg)

[0348] 2,5-di-tert-octylhydroquinone (50 mg)

[0349] red-sensitive silver chlorobromide emulsion (200 mg)

[0350] The top-most layer is prepared with and without a UV absorber:

[0351] With a UV Absorber

[0352] 2,5-di-tert-octylhydroquinone (20 mg)

[0353] hexyl5-[2,5-dihydroxy4-(4-hexyloxycarbpnyl-1,1-dimethylbutyl)phenyl]-5-methyl-hexanoate(20 mg)

[0354] gelatin (400 mg)

[0355] trinonyl phosphate (120 mg)

[0356] UV absorber test compound (385 mg)

[0357] Without a UV Absorber

[0358] gelatin (800 mg)

[0359] The hardener used is 2,4-dichloro-6-hydroxy-s-triazine potassiumsalt. The wetting agemt is the sodium salt ofdiisobutylhaphthalenesulfonic acid.

[0360] Three step wedges with a density difference of 0.3 log E per stepare exposed onto each of the samples (with blue, green and red light,respectively). The processing process RA-4 (Kodak) for color papers isthen carried out.

[0361] After exposure and processing, the reflectance densities in thered for the cyan step, in the green for the magenta step and in the bluefor the yellow step are measured at a density of between 0.9 and 1.1 ofthe wedges. The wedges are then exposed in an Atlas exposure instrumentat a total of 15 KJ/cm², and the reflectance densities are measuredagain.

[0362] In the case of the magenta wedge as well, the reflectance densitybefore and after exposure is measured in the blue for yellowing.

[0363] The presence of the instant UV absorbers reduces the dye densityloss of the cyan, magenta and yellow image dyes.

EXAMPLE 22 Photographic Compositions

[0364] The procedure described in Example 18 is repeated using a mixtureof 1 part by weight of an instant UV absorber and 1 part by weight of asecond instant UV absorber. Clear transparent coats are obtained whichare suitable for a photographic recording material.

EXAMPLE 23 Photographic Compositions

[0365] The procedure described in Example 18 is repeated using a mixtureof 1 part by weight of an instant UV absorber and 1 part by weight of asecond benzotriazole UV absorber. Clear transparent coats are obtainedwhich are suitable for a photographic recording material.

EXAMPLE 24 Automotive Coating Compositions

[0366] To ascertain the effect on thermal durability and loss rate froma high solids thermoset acrylic coating containing an instantbenzotriazole UV absorber, the following tests are carried out.

[0367] A high solids thermoset acrylic clear coat is prepared by mixingan experimental acrylic polyol resin and hexamethoxymethylmelamine(Resimene® 747, Monsanto) at a solids ratio of 60/40. The dodecylbenzenesulfonic acid catalyst (Nacure® 5225; King Industries) is added at 0.70%by weight. A flow aid Modaflow® (Monsanto) is added at 0.25% by weightto form a model acrylic melamine resin system.

[0368] The model clear coat is reduced with xylene to a viscosity of26-27 second using a Zahn #2 cup and applied via a conventional airspray at 50 psi (3.5 Kg/cm²) over a 1″×3″ (2.54 cm×7.62 cm) quartzslide. Cure is achieved by baking the slide for 30 minutes at 260° F.(127° C.). The clear coat is stabilized with 1% by weight of a hinderedamine light stabilizer,bis-(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate, (TINUVIN®123, Ciba). The various test benzotriazole UV absorbers are incorporatedat the 5 mmol % by weight in the clear coat. The film thickness on thequartz slides range from 1.15 to 1.41 mils (0.029 to 0.036 mm).

[0369] The films on the quartz slides are weathered according to thefollowing conditions in Xenon Arc Weather-Ometer with a controlledirradiance at 6500 W, using inner quartz and outer borosilicate S-typefilter. The irradiation cycle is as follows: 40 minutes of straightirradiation with no water spray, followed by 20 minutes of light plusfront spray, followed by 60 minutes of light irradiation and finally by60 minutes dart plus rear spray (condensation). The setting is at 0.55W/M² at 340 nm, 1.98 kJ/hour. In the light cycle the black paneltemperature is controlled at 70±2° C. The relative humidity in the lightcycle is in the range of 50-55% and in the dark cycle 100%. Theabsorbance of the long wavelength UV band as a function of Xenon arcweathering hours are recorded.

[0370] To follow the loss of UV absorbers from the clear coats, UVspectra are measured initially and after weathering at regular timeintervals. The UV spectrophotometer measures absorbance linearly up to5.5 absorbance units using a reference beam attenuation technique.

[0371] It is assumed that the degradation products from the UV absorberdo not contribute to the UV spectrum. This is tested by following theratio of absorbance of the band at about 300 nm and the band at about340 nm. The ratio does not change upon weathering the sample. Thissuggests that the UV spectrum of the weathered films correspond to theamount of UV absorber remaining in the film with very little if anycontribution to the spectrum by photo degradants.

[0372] Representative benzotriazole test compounds are incorporated intoa high solid thermoset acrylic melamine resin at a concentration of 3%by weight to give equal molar concentrations of the test benzotriazolein equal film thickness and sufficient to give a starting absorbance ofapproximately 2.0 absorbance units. The test samples are exposed for1026, 2025 and 3335 hours respectively. Compound of Units of AbsorbanceExample* Loss after 1026 hours TINUVIN ® 384 0.42 Example 5 0.18 Example14 0.11

[0373] Compound of Units of Absorbance Example* Loss after 2025 hoursTINUVIN ® 384 0.77 TINUVIN ® 928 0.43 Example 5 0.41 Example 14 0.20

[0374] Compound of Units of Absorbance Example* Loss after 3335 hoursTINUVIN ® 384 1.16 TINUVIN ® 928 0.69 Example 5 0.64 Example 14 0.30

[0375] The test shows that the instant benzotriazoles are especiallydurable in automotive coatings as judged by low loss rates.

EXAMPLE 25 Methyl3-(Benzotriazol-2-yl)-4-hydroxy-5-(1,1-diphenylethyl)hydrocinnamate

[0376] Following the general procedures of Examples 1-5, the titlecompound is prepared.

EXAMPLE 26 Methyl3-(5-Chloro-benzotriazol-2-yl)-4-hydroxy-5-(1,1-diphenylethyl)hydrocinnamate

[0377] Following the general procedures of Examples 1-5, the titlecompound is prepared.

EXAMPLE 27

[0378] Octyl3-(5-Chloro-benzotriazol-2-yl)-4-hydroxy-5-(1,1-diphenylethyl)hydrocinnamate

[0379] The compound prepared in Example 26 is refluxed in toluene in thepresence of lithium amide and EXXAL® 8 (mixture of octanols,Exxon-Mobil) for four hours. The title compound is obtained.

EXAMPLE 28 ω-Hydroxy-hepta-(ethyleneoxy)ethyl3-(Benzotriazol-2-yl)-4-hydroxy-5-(1,1-diphenylethyl)hydrocinnamate and3,6,9,12,15,18,21-HeptaoxatricosanyleneBis(3-(benzotriazol-2-yl)-4-hydroxy-5-(1,1-diphenylethyl)hydrocinnamate)

[0380] The methyl ester compound prepared in Example 25 is heated to170° C. in the presence of poly(ethylene glycol) (molecular weight 300,available from DOW) and dibutyltin oxide, under a full vacuum, for fourhours. The desired product which is a mixture of monomeric and dimericesters depending on the stoichiometry is obtained.

EXAMPLE 29 Methyl3-(5-Trifluoromethyl-benzotriazol-2-yl)-4-hydroxy-5-(1,1-diphenylethyl)hydrocinnamate

[0381] Following the general procedures of Examples 1-5, the titlecompound is prepared.

EXAMPLE 303-(5-Trifluoromethyl-benzotriazol-2-yl)-4-hydroxy-5-(1,1-diphenylethyl)hydrocinnamicAcid

[0382] The title compound is prepared by refluxing the compound preparedin Example 29 in aqueous sodium hydroxide solution followed byneutralization with aqueous hydrochloric acid.

EXAMPLE 31 3-Methacryloyloxy-2-hydroxypropyl3-(5-Trifluoromethyl-benzotriazol-2-yl)-4-hydroxy-5-(1,1-diphenylethyl)hydrocinnamateand 3-Methacryloyloxy-1-hydroxyprop-2-yl3-(5-Trifluoromethyl-benzotriazol-2-yl)-4-hydroxy-5-(1,1-diphenylethyl)hydrocinnamate

[0383] The desired mixture of the title compounds is obtained when theinstant compound of Example 30, toluene, tetrabutylammonium bromide andglycidyl methacrylate are heated to 105° C. and held there for fourhours. After cooling the reaction mixture to 80° C., washing thrice withwater, the toluene is removed by vacuum distillation to give the desiredmixture of title compounds.

EXAMPLES 32-50

[0384]

[0385] Following the general procedures of Examples 1-5, the compoundsare prepared as represented by formula I (above) where E₁ is1,1-diphenylethyl in all examples. Example G₁ G₂ E₂ G₃ or E₃ E₆ or E₈ 32Cl Cl t-butyl — — 33 F F octyl — — 34 H F t-butyl — — 35 H F EtCOOE₆ —methyl 36 H F EtCONHE₈ — octadecyl 37 H * dodecyl — — 38 H ** octadecylethyl — 39 H *** t-butyl methyl — 40 H ** t-butyl octyl — 41 H ****octyl octadecyl — 42 H E₃SO t-butyl phenyl — 43 H E₃SO₂ methyl butyl —44 H E₃SO₂ methyl octadecyl — 45 H CF₃ methyl — — 46 H CF₃ EtOH — — 47 HCF₃ EtOAl — — 48 H CF₃ EtCOOE₆ — octyl 49 H CF₃ EtCOOE₆ — methyl 50 HCF₃ EtCONHE₈ — octadecyl

EXAMPLE 51 Poly(methyl methacrylate)

[0386] Poly(methyl methacrylate), medium molecular weight, Aldrich, isdissolved in methylene chloride at room temperature along with between 1and 3% by weight of test benzotriazole, based on the PMMA resin. Filmsare cast using a calibrated drawdown bar to prepare 1 mil thick filmafter drying. The free standing films are mounted into cardboardholders, secured in metal frames and exposed in an Atlas C165 Xenon-arcWeather-Ometer under dry conditions according to ASTM G26. Performanceis measured by a change in color or the physical integrity of the film,or in loss of absorbance of the UV absorber at λmax. Color measurementsare carried out in an ACS spectrophotometer, small area view, spectralcomponent included d/8, D65, 100 observer, YI 1925 for unexposed andexposed samples after 1000 hours exposure. Compound of Example* (% byweight) ΔYI TINUVIN ® 234 (2.50%) 1.26 Example 9 (2.69%) 0.96 Example 14(3.19%) 0.97

[0387] These data show that the instant compounds are particularlyefficacious when used in thermoplastic compositions, such as poly(methylmethacrylate), even surpassing a commerical UV absorber ineffectiveness. This is shown by the reduction of yellowing (ΔYI) afterexposure to actinic radiation.

EXAMPLE 52 1,1-bis(4-methoxyphenyl)ethylene

[0388] An equivalent of methyl magnesium bromide/diethyl ether solutionis reacted with 4,4′-dimethoxybenzophenone (24.2 g, 0.1 mol) dissolvedin anhydrous diethyl ether over a 60 minute period at ambienttemperature. The reaction mixture is poured onto ice and extracted withether. The ether is removed by distillation and replaced with ethylacetate (100 mL). The ethyl acetate solution is refluxed for one hourover anhydrous magnesium sulfate. Methylene chloride (300 mL) is addedand the magnesium sulfate removed by filtration. The solvent isdistilled leaving 16.9 g of the title compound as a white solid meltingat 137° C. whose structure is consistent with ¹Hnmr and massspectrometry.

EXAMPLE 532-[2-Hydroxy-3-[1,1-di(4-methoxyphenyl)ethyl]-5-tert-butylphenyl]-2H-benzotriazole

[0389] Starting with the compound of Example 52 and following thegeneral procedures of Examples 1-5, the title compound is prepared.

EXAMPLES 54-70

[0390] Following the general procedures outlined in Examples 52 and 1-5,the compounds of formula I

[0391] where G₁ is hydrogen, G₂ is hydrogen, E₂ is tert-butyl and E₁ isa group of formula IV

[0392] shown in the following table are prepared.

[0393] In the compounds in the table below, E₂₃, E₂₅, E₂₆, E₂₈, E₂₉, E₃₁and E₃₂ are always hydrogen except as indicated. In Example 56, E₂₆,E₂₈, and E₃₂ are each methyl; and in Example 58, E₂₃, E₂₅, E₂₉ and E₃₁are each chloro. Example E₂₂ E₂₄ E₂₇ E₃₀ 54 H allyloxy ethyl allyloxy 55F H methyl H 56 methyl methyl n-butyl methyl 57 F F methyl H 58 H Hmethyl H 59 H CF₃ methyl CF₃ 60 H acetyl methyl acetyl 61 H -COOCH₃methyl -COOCH₃ 62 H MACOO- methyl MACOO- 63 H H octadecyl StCONH- 64 Hcyano methyl cyano 65 H EtNHCO- methyl EtNHCO- 66 H C₆H₅SO₂- methylC₆H₅SO₂- 67 H CH₃S- methyl CH₃S- 68 H EtNHSO₂- methyl EtNHSO₂- 69 H OHmethyl OH 70 H -COOH methyl -COOH

EXAMPLE 712-{2-Hydroxy-3-[1,1-di(4-(2-hydroxyethoxy)phenyl)ethyl]-5-tert-butylphenyl}-2H-benzotriazole

[0394] When the compound of instant Example 69 is reacted with ethylenecarbonate, the title compound is prepared.

EXAMPLE 722-{2-Hydroxy-3-[1,1-di(4-(2-bromoethoxy)phenyl)ethyl]-5-tert-butylphenyl}-2H-benzotniazole

[0395] When the compound of instant Example 71 is reacted withhydrobrornic acid according to the procedure given in Brown & Patai,“The Chemistry of the Hydroxyl Group”, Part 1, pages 595-622, the titlecompound is prepared.

EXAMPLE 732-{2-Hydroxy-3-[1,1-di(4-(2-phthalimidoethoxy)phenyl)-ethyl]-5-tert-butylphenyl}-2H-benzotriazole

[0396] When the compound of instant Example 72 is treated with potassiumphthalimide according to Gibson & Bradshaw, Ange. Chem. Int. Ed. Engl.,7, 919-930 (1968), the title compound is prepared.

What is claimed is:
 1. A benzotriazole compound of formula I, II or III

wherein G₁ is hydrogen or chloro, G₂ is hydrogen, cyano, perfluoroalkylof 1 to 12 carbon atoms, halogen, —CO—G₃, —COOG₃, —CONHG₃, —CON(G₃)₂,E₃SO—, E₃SO₂—, nitro, —P(O)(C₆H₅)₂, —P(O)(OG₃)₂,

G₃ is hydrogen, straight or branched chain alkyl of 1 to 24 carbonatoms, straight or branched chain alkenyl of 2 to 18 carbon atoms,cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms,phenyl, or said phenyl or said phenylalkyl substituted on the phenylring by 1 to 4 alkyl of 1 to 4 carbon atoms, E₁ is hydrogen, straight orbranched chain alkyl of 1 to 24 carbon atoms, straight or branched chainalkenyl of 2 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms,phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or saidphenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4carbon atoms; or E₁ is alkyl of 1 to 24 carbon atoms substituted by oneor two hydroxy groups; or E₁ is alkyl of 1 to 24 carbon atoms, alkenylof 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by oneor more —OCOE₁₁, —OE₄, —NCO, —NHCOE₁₁, or —NE₇E₈, or mixtures thereof,where E₄ is straight or branched chain alkyl of 1 to 24 carbon atoms orstraight or branched chain alkenyl of 2 to 18 carbon atoms; or saidalkyl or said alkenyl interrupted by one or more —O—, —NH— or —NE₄—groups or mixtures thereof and which can be unsubstituted or substitutedby one or more —OH, —OE₄ or —NH₂, or mixtures thereof; or E₁ is a groupof formula IV

where E₂₂, E₂₃, E₂₄, E₂₅, E₂₆, E₂₈, E₂₉, E₃₀, E₃₁ and E₃₂ areindependently hydrogen, halogen, straight or branched alkyl of 1 to 18carbon atoms, alkenyl of 2 to 18 carbon atoms, said alkyl or saidalkenyl substituted by one or more halogen, —OCOE₁₁, —OE₄, —NCO,—NHCOE₁₁ or —NE₇E₈, or mixtures thereof, where E₄ is straight orbranched chain alkyl of 1 to 24 carbon atoms or straight or branchedchain alkenyl of 2 to 18 carbon atoms; or said alkyl or said alkenylinterrupted by one or more —O—, —NH— or —NE₄— groups or mixtures thereofand which can be unsubstituted or substituted by one or more —OH, —OE₄or —NH₂, or mixtures thereof; or E₂₂, E₂₃, E₂₄, E₂₅, E₂₆, E₂₈, E₂₉, E₃₀,E₃₁ and E₃₂ are independently phenyl, —OH, —OCOE₁₁, —OE₃₃, —NCO,—NHCOE₁₁ or —NE₇E₈, cyano, nitro, peffluoroalkyl of 1 to 12 carbonatoms, —COG₃, —COOG₃, —CON(G₃)₂, —CONHG₃, E₃S—, E₃SO—, E₃SO₂—,—P(O)(C₆H₅)₂, —P(O))OG₃)₂, —SO₂—X₁—E₃₃; X₁ is —O—, —NH— or —NE₄—; E₂₇ isalkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms orphenyl, E₃₃ is straight or branched chain alkyl of 1 to 24 carbon atoms,straight or branched chain alkenyl of 2 to 18 carbon atoms, said alkylor said alkenyl substituted by one or more —OH, —OCOE₁₁, —OE₄, —NCO,—NHCOE₁₁, —NE₇E₈, phthalimido,

or mixtures thereof, where E₄ is straight or branched chain alkyl of 1to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms; or said alkyl orsaid alkenyl interrupted by one or more —O—, —NH— or —NE₄— groups ormixtures thereof and which can be unsubstituted or substituted by one ormore —OH, —OE₄ or —NH₂, or mixtures thereof; or E₃₃ is phenyl orphenylalkyl of 7 to 15 carbon atoms, or said phenyl or said phenylalkylsubstituted by one to three alkyl groups of 1 to 4 carbon atoms; E₂ isstraight or branched alkyl chain of 1 to 24 carbon atoms, straight orbranched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or saidphenyl or said phenylalkyl substituted on the phenyl ring by one tothree alkyl of 1 to 4 carbon atoms; or E₂ is alkyl of 1 to 24 carbonatoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more—OH, —OCOE₁₁, —OE₄, —NCO, —NH₂, —NHCOE₁₁, —NHE₄ or —N(E₄)₂, or mixturesthereof, where E₄ is straight or branched chain alkyl of 1 to 24 carbonatoms; or said alkyl or said alkenyl interrupted by one or more —O—,—NH— or —NE₄— groups or mixtures thereof and which can be unsubstitutedor substituted by one or more —OH, —OE₄ or —NH₂ groups or mixturesthereof; or E₂ is a group of formula IV described above; n is 1 or 2,when n is 1, E₅ is OE₆ or NE₇E₈, or E₅ is —PO(OE₁₂)₂, —OSi(E₁₁)₃ or—OCO—E₁₁, or straight or branched chain C₁-C₂₄alkyl which is interruptedby —O—, —S— or —NE₁₁ and which can be unsubstituted or substituted by—OH or —OCO—E₁₁, C₅-C₁₂ cycloalkyl which is unsubstituted or substitutedby —OH, straight chain or branched C₂-C₁₈alkenyl which is unsubstitutedor substituted by —OH, C₇-C₁₅aralkyl, —CH₂—CHOH-E₁₃ or glycidyl, E₆ ishydrogen, straight or branched chain C₁-C₂₄alkyl which is unsubstitutedor substituted by one or more OH, OE₄ or NH₂ groups, or —OE₆ is—(OCH₂CH₂)_(w)OH or —(OCH₂CH₂)WOE₂₁ where w is 1 to 12 and E₂₁ is alkylof 1 to 12 carbon atoms, E₇ and E₈ are independently hydrogen, alkyl of1 to 18 carbon atoms, straight or branched chain C₃-C₁₈alkyl which isinterrupted by —O—, —S— or —NE₁₁—, C₅-C₁₂cycloalkyl, C₆-C₁₄aryl orC₁-C₃hydroxylalkyl, or E₇ and E₈ together are alkylene of 4 to 6 carbonatoms, 3-oxapentamethylene, 3-iminopentamethylene or3-methyliminopentamethylene, or E₅ is —X—(Z)_(p)—Y—E₁₅ wherein X is −O—or —N(E₁₆)—, Y is −O— or —N(E₁₇)—, Z is C₂-C₁₂-alkylene, C₄-C₁₂-alkyleneinterrupted by one to three nitrogen atoms, oxygen atoms or a mixturethereof, or is C₃-C₁₂-alkylene, butenylene, butynylene, cyclohexylene orphenylene, each substituted by a hydroxyl group, m is zero, 1 or 2, p is1, or p is also zero when X and Y are —N(E₁₆)— and —N(E₁₇)—,respectively, E₁₅ is a group —CO—C(E₁₈)═C(H)E₁₉ or, when Y is —N(E₁₇)-,forms together with E₁₇ a group —CO—CH═CH—CO—, wherein E₁₈ is hydrogenor methyl, and E₁₉ is hydrogen, methyl or —CO—X—E₂₀, wherein E₂₀ ishydrogen, C₁-C₁₂-alkyl or a group of the formula

wherein the symbols E₁, G₂, X, Z, m and p have the meanings definedabove, and E₁₆ and E₁₇ independently of one another are hydrogen,C₁-C₁₂-alkyl, C₃-C₁₂-alkyl interrupted by 1 to 3 oxygen atoms, or iscyclohexyl or C₇-C₁₅aralkyl, and E₁₆ together with E₁₇ in the case whereZ is ethylene, also forms ethylene, when n is 2, E₅ is one of divalentradicals —O—E₉—O— or —N(E₁₁)—E₁₀—N(E₁₁)—, E₉ is C₂-C₈alkylene,C₄-C₈alkenylene, C₄alkynylene, cyclohexylene, straight or branched chainC₄-Cloalkylene which is interrupted by —O— or by—CH₂—CHOH—CH₂—O—E₁₄—O—CH₂—CHOH—CH₂—, E₁₀ being straight or branchedchain C₂-C₁₂alkylene which may be interrupted by —O—, cyclohexylene, or

or E₁₀ and E₁₁ with the two nitrogen atoms form a piperazine ring, E₁₄is straight or branched chain C₂-C₈alkylene, straight or branched chainC₄-C₁₀alkylene which is interrupted by —O—, cycloalkylene, arylene or

E₁₁ is hydrogen, straight or branched chain C₁-C₁₈alkyl,C₅-C₁₂cycloalkyl, straight or branched chain C₂-C₁₈alkenyl, C₆-C₁₄arylor C₇-C₁₅aralkyl, E₁₂ is straight or branched chain C₁-C₁₈alkyl,straight or branched chain C₃-C₁₈alkenyl, C₅-C₁₀cycloalkyl, C₆-C₁₆arylor C₇-C₁₅aralkyl, E₁₃ is H, straight chain or branched C₁-C₁₈alkyl whichis substituted by —PO(OE₁₂)₂, phenyl which is unsubstituted orsubstituted by OH, C₇-C₁₅aralkyl or —CH₂OE₁₂, E₃ is alkyl of 1 to 20carbon atoms, hydroxyalkyl of 2 to 20 carbon atoms, alkenyl of 3 to 18carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted byone or two alkyl of 1 to 4 carbon atoms or1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6to 16 carbon atoms, T is —SO—, —SO₂—, —SO—E—SO—, —SO₂—E—SO₂—, —CO—,—CO—CO—, —CO—CH₂—CO—, —CO—E—CO—, —COO—E—OCO— or —CO—NG₅—E—NG₅—CO—, whereE is alkylene of 2 to 12 carbon atoms, cycloalkylene of 5 to 12 carbonatoms, or alkylene interrupted or terminated by cyclohexylene of 8 to 12carbon atoms; G₅ is G₃ or hydrogen, and with the proviso that at leastone of E₁ and E₂ Must contain a group of formula IV; and with thefurther proviso that when E₂₄ and E₃₀ are OH, G₂ is not hydrogen.
 2. Acompound according to claim 1 of formula I

wherein G₁ is hydrogen, G₂ is hydrogen, cyano, CF₃—, fluoro, chloro,—CO—G₃, —COOG₃ or E₃SO₂—, G₃ is straight or branched chain alkyl of 1 to24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbonatoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbonatoms, phenyl, or said phenyl or said phenylalkyl substituted on thephenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E₁ is a group offormula IV wherein E₂₂, E₂₃, E₂₄, E₂₅, E₂₆, E₂₈, E₂₉, E₃₀, E₃₁ and E₃₂are hydrogen, and E₂₇ is methyl, E₂ is straight or branched alkyl chainof 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted onthe phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms; or E₂ is saidalkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atomssubstituted by one or more —OH, —OCOE₁₁, —OE₄, —NCO, —NH₂, —NHCOE₁₁,—NHE₄ or —N(E₄)₂, or mixtures thereof, where E₄ is straight or branchedchain alkyl of 1 to 24 carbon atoms; or said alkyl or said alkenylinterrupted by one or more —O—, —NH— or —NE₄— groups or mixtures thereofand which can be unsubstituted or substituted by one or more —OH, —OE₄or —NH₂ groups or mixtures thereof, or E₂ is a group of formula IVwherein E₂₂, E₂₃, E₂₄, E₂₅, E₂₆, E₂₈, E₂₉, E₃₀, E₃₁, and E₃₂ arehydrogen, alkyl of 1 to 12 carbon atoms, straight or branched chainalkenyl of 2 to 18 carbon atoms, OH, cyano, —OE₃₃, chloro, fluoro,—OCOE₁₁, CF₃, —COOG₃, E₃S—, E₃SO₂— or —SO₂—NH—E₃₃; and E₂₇ is methyl, E₃is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon atoms,alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms,phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms orsaid aryl substituted by one or two alkyl of 1 to 4 carbon atoms or1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6to 16 carbon atoms; and wherein E₁₁ and E₃₃ are as defined above.
 3. Acompound according to claim 1 which is (a)2-[2-hydroxy-3-(1,1-diphenylethyl)-5-tert-butylphenyl]-2H-benzotriazole;(b)5-chloro-2-[2-hydroxy-3-(1,1-diphenylethyl)-5-tert-butylphenyl]-2H-benzo-triazole;or (c)5-trifluoromethyl-2-[2-hydroxy-3-(1,1-diphenylethyl)-5-tert-octylphenyl]-2H-benzotriazole.4. A stabilized composition which comprises (a) an organic materialsubject to degradation by heat, light or oxygen, and (b) an effectivestabilizing amount of a compound of formula I, II or III according toclaim
 1. 5. A composition according to claim 4 wherein component (a) isa thermoplastic polyolefin, polyester, polyester urethane, polyetherurethane or a water-borne coating.
 6. A composition according to claim 5wherein component (a) is selected from the group consisting ofpolypropylene, thermoplastic polyolefin, low density polyethylene,medium density polyethylene, high density polyethylene, linear lowdensity polyethylene, poly(butene-1), ethylene/vinyl acetate copolymer,ethylene/propylene copolymer, copolymers of ethylene or propylene withother alpha-olefins, copolymers of acrylonitrile-butadiene-styrene(ABS), copolymers of acrylonitrile and styrene that are impact modifiedwith ethylene-propylene rubber or ethylene/propylene/alpha-olefin rubberor butyl acrylate rubber, blends of ABS and polycarbonate, blends of ABSand poly(vinyl chloride) (PVC), poly(vinyl chloride), copolymers ofstyrene and butadiene (HIPS), copolymers of styrene and butadiene thatalso contain ethylene-propylene rubber orethylene/propylene/alpha-olefin rubber or butyl acrylate rubber,thermoplastic elastomers and thermoplastic vulcanizates.
 7. Acomposition according to claim 5 wherein component (a) is a polyester orpolyether urethane or water-borne coating.
 8. A composition according toclaim 6 which additionally contains an effective stabilizing amount ofat least one coadditive stabilizer selected from the group consisting ofthe phenolic antioxidants, metal stearates, metal oxides,organophosphorus compounds, furanone antioxidants, hydroxylamines, UVabsorbers, non-NOR hindered amines, NOR hindered amines and mixturesthereof.
 9. A composition according to claim 6 which additionallycontains a filler.
 10. A composition according to claim 9 wherein thefiller is calcium carbonate, clay, talc, mica or glass.
 11. Acomposition according to claim 6 wherein component (a) is a polyolefinfilm, fiber or thick section, ABS, high impact polystyrene (HIPS),thermoplastic polyolefin, thermoplastic elastomer or thermoplasticvulcanizate which additionally contains a halogenated flame retardant.12. A composition according to claim 11 wherein the flame retardant istris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate, decabromodiphenyloxide, ethylene bis(tetrabromophthalimide) or ethylenebis(dibromonorbornanedicarboximide).
 13. A composition according toclaim 6 wherein component (a) is polypropylene fiber.
 14. A compositionaccording to claim 6 wherein component (a) is polypropylene,polyethylene or thermoplastic polyolefin (TPO).
 15. A compositionaccording to claim 14 wherein component (a) is a paintable thermoplasticolefin (TPO).
 16. A composition according to claim 4 which additionallycomprises a coadditive stabilizer which is a hindered phenolicantioxidant selected from the group consisting of neopentanetetrayltetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate, octadecyl3,5-di-tert-butyl-4-hydroxyhydrocinnamate,1,3,5-trimethyl-2,4,6-tris(3,5,-di-tert-butyl-4-hydroxybenzyl)benzene,1,2-bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)hydrazine, calcium[bis(monoethyl 3,5-ditert-butyl-4-hydroxybenzyl)phosphonate],1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate and1,3,5-tris(3-hydroxy-4-tert-butyl-2,6-dimethylbenzyl) isocyanurate; oris an organophosphorus stabilizer selected from the group consisting oftris(2,4-di-tert-butylphenyl) phosphite,bis(2,4-di-tert-butyl-6-methyl-phenyl) ethyl phosphite,2,2′,2″-nitrilo[triethyl-tris-(3,3′,5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl)phosphite], tetrakis(2,4-di-butylphenyl) 4,4′-biphenylene-diphosphonite,tris(nonylphenyl) phosphite, bis(2,4-di-tert-butylphenyl)pentaerythrityl diphosphite, 2,2′-ethylidenebis(2,4-di-tert-butylphenyl)fluorophosphite and 2-butyl-2-ethylpropan-1,3-diyl2,4,6-tri-tert-butylphenyl phosphite; or is5,7-di-tert-butyl-3-(3,4-dimethylphenyl)-2H-benzofuran-2-one; or isN,N-dialkylhydroxylamine made by the direct oxidation ofN,N-di(hydrogenated tallow)amine; or is a hindered amine selected fromthe group consisting of bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate,the polycondensation product of1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinicacid,N,N′,N″,N′″-tetrakis[4,6-bis(butyl-1,2,2,6,6-pentamethylpiperidin-4-yl)amino-s-triazin-2-yl]-1,10-diamino-4,7-diazadecane,the polycondensation product of4,4′-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and2,4-dichloro-6-tert-octyl-amino-s-triazine, the polycondensation productof 4,4′-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and2,4-dichloro-6-morpholino-s-triazine, the polycondensation product of4,4′-hexamethylenebis(amino-1,2,2,6,6-pentamethylpiperidine) and2,4-dichloro-6-morpholino-s-triazine, 2,2,6,6-tetramethylpiperidin-4-yloctadecanoate,3-dodecyl-1-(1-acetyl-2,2,6,6-tetramethylpiperidin-4-yl)-pyrrolidin-2,5-dione,1,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino}-s-triazine,poly[methyl 3-(2,2,6,6-tetramethylpiperidin-4-yloxy)propyl]siloxane, thepolycondensation product of2,4-dichloro-6-(2,2,6,6-tetramethylpiperidin-4-yl)butyl-amino)-s-triazine,2,2′ethylene-bis{[2,4-(2,2,6,6-tetramethylpiperidin-4-yl)butylamino-s-triazin-6-yl]aminotrimethyleneamino},oligomer ofN-{[2-(N-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamineterminated with 2,4-bis(dibutylamino)-s-triazin-6-yl,N,N′,N″-tris{2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine,N,N′,N′″-tris {2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamineand N,N′,N″,N′″-tetrakis {2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine; or is another N-hydrocarbyloxysubstituted hindered amines selected from the group consisting ofbis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate,bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) adipate,bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) adipate,bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate,1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl octadecanoate,N,N′,N″-tris(2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-6-yl1-3,3′-ethylenediiminodipropylamine, N,N′,N′″-tris{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine and N,N′,N″,N′″-tetrakis{2,4-bis[N-(1-cyclohexyl-oxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediimino-dipropylamine;or a hydroxy substituted N-hydrocarbyloxy substituted hindered amineselected from the group consisting ofbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetra-methylpiperidin-4-yl)]sebacate; a mixture ofbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate andbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]adipate;1-(2-hydroxy-2-methylpropoxy)-4-octa-decanoyloxy-2,2,6,6-tetramethylpiperidine;bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]adipate;bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate;bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]succinate; a mixture ofbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate andbis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]succinate;1-(4-octadecanoyloxy-2,2,6,6-tetramethylpiperidin-1-yloxy)-2-octadecanoyloxy-2-methylpropane;1-(2-hydroxy-2-methylpropoxy)-4-[9-(methoxy-carbonyl)nonanoyloxy]-2,2,6,6-tetramethylpiperidine;1-(2-hydroxy-2-methylpropoxy)-4-[5-(methoxy-carbonyl)pentanoyloxy]-2,2,6,6-tetramethylpiperidine;1-(2-hydroxy-2-methylpropoxy)-4-[3-(methoxy-carbonyl)-propionyloxy]-2,2,6,6-tetramethylpiperidine;1-(2-hydroxy-2-methylpropoxy)-4-[4-(methoxy-carbonyl)butyryloxy]-2,2,6,6-tetramethylpiperidine;or is a UV absorber selected from the group consisting of2-(2-hydroxy-3,5-di-α-cumylphenyl)-2H-benzo-triazole,2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole,5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole,2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole,2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzotriazole,2,4-di-tert-butylphenyl 3,5-di-tert-butyl4-hydroxybenzoate,2-hydroxy-4-n-octyloxybenzophenone,2,4-bis(2,4-dimethyphenyl)-(2-hydroxy-4-octyloxyphenyl)-s-triazine,oligomer ofN-{2-[(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′-bis(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamineterminated with 2,4-bis(dibutylamino)-s-triazin-6-yl, the condensationproduct of 2-morpholino-4,6-dichloro-s-triazine withN,N′-bis(1,2,2,6,6-pentamethylpiperidin-4-yl)-1,6-hexanediamine; ormixtures thereof.
 17. A composition according to claim 16 wherein thecoadditive stabilizer is neopentanetetrayltetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate,tris(2,4-di-tert-butylphenyl) phosphite, N,N-dialkylhydroxylamine madeby the direct oxidation of N,N-di(hydrogenated tallow)amine,N,N′,N″,N′″-tetrakis[4,6-bis(butyl-1,2,2,6,6-pentamethylpiperidin-4-yl)amino-s-triazin-2-yl]-1,10-diamino-4,7-diazadecane,the polycondensation product of4,4′-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and2,4-dichloro-6-tert-octylamino-s-triazine, the polycondensation productof 4,4′-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and2,4-dichloro-6-morpholino-s-triazine, the polycondensation product of4,4′-hexamethylenebis(amino-1,2,2,6,6-pentamethylpiperidine) and2,4-dichloro-6-morpholino-s-triazine, oligomer ofN-{[2-(N-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′-bis(2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamineterminated with 2,4-bis(dibutylamino)-s-triazin-6-yl,N,N′,N″-tris{2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine,N,N′,N′″-tris{2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine and N,N′,N″,N′″-tetrakis{2,4-bis[N-(1,2,2,6,6pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′-ethylenediiminodipropylamine,oligomer ofN-{2-[(1-propoxy-2,2,6,6-tetramethylpiperidin4-yl)butylamino]-s-triazin-4-yl}-N,N′-bis(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamineterminated with 2,4-bis(dibutyl-amino)-s-triazin-6-yl, or thecondensation product of 2-morpholino-4,6-dichloro-s-triazine withN,N′-bis(1,2,2,6,6-pentamethylpiperidin-4-yl)-1,6-hexanediamine.
 18. Acomposition according to claim 4 which additionally contains another UVabsorber selected from the group consisting of the benzotriazoles, thes-triazines, the oxanilides, the salicylates, the hydroxybenzophenones,the benzoates and the α-cyanoacrylates.
 19. A composition according toclaim 4 which additionally contains a UV absorber selected from thegroup consisting of (a)5-trifluoromethyl-2-(2-hydroxy-3-α-cumyl-5-tert-octylphenyl)-2H-benzo-triazole;(b) 5-trifluoromethyl-2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole;(c)5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole;(d)2,2′-methylene-bis[6-(5-trifluoromethyl-2H-benzotriazol-2-yl)-4-tert-octyl-phenol];(e)methylene-2-[4-tert-octyl-6-(2H-benzotriazol-2-yl)phenol]2′-[4-tert-octyl-6-(5-trifluoromethyl-2H-benzotriazol-2-yl)phenol];(f)3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-hydrocinnamicacid; (g) methyl3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-hydrocinnamate;(h) isooctyl3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate;(i)5-trifluoromethyl-2-[2-hydroxy-5-(3-hydroxypropyl)phenyl]-2H-benzotriazole;(j)5-trifluoromethyl-2-[2-hydroxy-5-(3-acryloyloxypropyl)phenyl]-2H-benzo-triazole;(k)5-trifluoromethyl-2-[2-hydroxy-5-(3-methacryloyloxypropyl)phenyl]-2H-benzotriazole;(l)5-trifluoromethyl-2-[2-hydroxy-5-(3-acrylylaminopropyl)phenyl]-2H-benzo-triazole;(m)5-trifluoromethyl-2-[2-hydroxy-5-(3-methacrylylaminopropyl)phenyl]-2H-benzotriazole;(n)5-trifluoromethyl-2-(2-hydroxy-3-α-cumyl-5-tert-butylphenyl)-2H-benzo-triazole;(o)5-trifluoromethyl-2-(2-hydroxy-3-α-cumyl-5-nonylphenyl)-2H-benzotriazole;(p)5-trifluoromethyl-2-[2-hydroxy-3-α-cumyl-5-(2-hydroxyethyl)phenyl]-2H-benzotriazole;(q)5-trifluoromethyl-2-[2-hydroxy-3-α-cumyl-5-(3-hydroxypropyl)phenyl]-2H-benzotriazole;(r)5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole;(s)5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;(t)5-trifluoromethyl-2-(2-hydroxy-3-dodecyl-5-methylphenyl)-2H-benzotriazole;(u)5-trifluoromethyl-2-[2-hydroxy-3-tert-butyl-5-(3-hydroxypropyl)phenyl)-2H-benzotriazole,(v)5-trifuoromethyl-2-[2-hydroxy-3-tert-butyl-5-(2-hydroxyethyl)phenyl]-2H-benzotriazole;(w)5-trifluoromethyl-2-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-2H-benzotriazole;(x)5-trifluoromethyl-2-(2-hydroxy-3,5-di-α-cumylphenyl)-2H-benzotriazole;(y) 5-fluoro-2-(2-hydroxy-3,5-di-α-cumylphenyl)-2H-benzotriazole; (z)5-butylsulfonyl-2-(2-hydroxy-3,5-di-α-cumylphenyl)-2H-benzotriazole;(aa)5-butylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;(bb)5-butylsulfonyl-2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole;and (cc)5-phenylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole.20. A composition according to claim 4 which is a stabilized stovinglacquer wherein component (a) is an acid catalyzed resin based on hotcrosslinkable, acrylic, acrylic melamine, polyester, polyurethane,polyamide or alkyd resin.
 21. A composition according to claim 20 whichadditionally contains a UV absorber selected from the group consistingof the benzotriazoles, the s-triazines, the oxanilides, the salicylates,the hydroxybenzophenones, the benzoates and the α-cyanoacrylates.
 22. Acomposition according to claim 20 which is an enamel of high solidscontent for industrial finishes.
 23. A composition according to claim 22which is a finishing enamel for automobiles.
 24. A composition accordingto claim 4 which is a stabilized ambient curable composition whereincomponent (a) is a resin selected from the group consisting ofunmodified or modified alkyd resin, acrylic resin, acrylic alkyd resin,polyester resin or crosslinkable epoxide resin.
 25. A compositionaccording to claim 24 wherein the resin is selected from the groupconsisting of unmodified alkyl, acrylic, acrylic alkyd or polyesterresins; said resins modified with silicon, isocyanates, isocyanurates,ketimines or oxazolidines; crosslinked epoxy resins; andepoxy-crosslinked acrylic and polyester resins.
 26. A compositionaccording to claim 25 which is an enamel of high solids content forindustrial finishes.
 27. A composition according to claim 26 which is afinishing enamel for automobiles.
 28. A composition according to claim27 which is a curable electrocoat composition wherein component (a) isan amino-group containing resin having functional groups that arereactive with an isocyanate and an aromatic polyisocyanate crosslinkingagent.
 29. A composition according to claim 4 which is a non-gellingliquid coating composition wherein component (a) comprises (A) at leastone acrylic monomer, (B) silica and (C) at least one initiator forultraviolet radication-induced curing of said composition.
 30. Acomposition according to claim 29 which contains a silyl acrylate, apolyfunctional acrylate, silica and a photoinitiator.
 31. A compositionaccording to claim 4 wherein component (a) is a polyolefin,polycarbonate, a styrenic, ABS, a nylon (polyamide), a polyester, apolyurethane, a polyacrylate, a rubber modified styrenic, poly(vinylchloride), poly(vinyl butyral), polyacetal (polyoxymethylene), or otherblends or copolymers such as poly(ethylene/1,4-cyclohexylenedimethyleneterephthalate) PETG or an ethylene/acrylic acid copolymer or saltsthereof (an ionomer).
 32. A composition according to claim 31 whereinthe polymer is a polyester or a polyacrylate.
 33. A compositionaccording to claim 32 wherein the polyester is poly(ethyleneterephthalate), poly(butylene terephthalate) or poly(ethylenenaphthalenedicarboxylate), or copolymerpoly(ethylene/1,4-cyclohexylenedimethylene terephthalate) PETG.
 34. Acomposition according to claim 4 wherein component (a) is athermoplastic polymer.
 35. A composition according to claim 34 whereinthe polymer is a polyolefin or polycarbonate.
 36. A compositionaccording to claim 35 wherein the polymer is polyethylene orpolypropylene.
 37. A composition according to claim 4 wherein component(a) is a photographic composition.
 38. A composition according to claim35 wherein the polymer is polycarbonate.
 39. A composition according toclaim 32 wherein the polymer is a polyacrylate.
 40. A compositionaccording to claim 39 wherein the polyacrylate is poly(methylmethacrylate).